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Journal articles on the topic 'Organic synthesis ; organometallic chemistry ; transition metal catalysis'

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Published: 4 June 2021

Last updated: 3 February 2022

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1

Dong, Zhi-Bing, and Jin-Quan Chen. "Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions." Synthesis 52, no. 24 (2020): 3714–34. http://dx.doi.org/10.1055/s-0040-1706550.

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AbstractOrganometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organozinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

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2

Alexakis, Alexandre. "Preface." Pure and Applied Chemistry 78, no. 2 (2006): vi. http://dx.doi.org/10.1351/pac20067802vi.

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The 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13<http://omcos13.unige.ch/>) was held in Geneva, Switzerland, from 17-21 July 2005.The aim of this series of symposia is to bring together chemists from academia and industry to define and discuss the most recent developments in the areas of catalysis, new organometallic reagents and reactions, and new materials chemistry. In 2001, Sharpless, Noyori, and Knowles received the Nobel Prize for their work in this area of chemistry; and the high profile has been maintained by the award of the 2005 Nobel Prize in Chemistry to Chauvin, Grubbs, and Schrock for the development of the metathesis method in organic synthesis.OMCOS-13 had a record number of nearly 1200 participants from 41 countries, and there was an encouragingly high proportion of young scientists in attendance. Very strong Asian participation at this conference reflected the outstanding level of research and leadership in this field from countries such as Japan, China, South Korea, and Taiwan.Prof. Shengming Ma, from the Shanghai Institute of Organic Chemistry of the Chinese Academy of Science and the Department of Chemistry, Zhejiang University, China received the OMCOS-13 Award (sponsored by the Yen Chuang Foundation and Springer Verlag). The prize was awarded for his creative research contributions in the field of transition-metal-catalyzed reactions of allenes.Apart from the OMCOS-13 Award lecture, there were 23 plenary lectures and 20 oral communications that dealt with aspects of reactivity and chemoselectivity of main group and transition-metal organometallics. Stereoselectivity issues also figured prominently with a particular emphasis on asymmetric synthesis and catalysis. Mechanistic insights, new reagents for synthesis, new catalyst and ligand design, and ligand effects were other important topics.The quality of the 620 posters that were on display during the entire conference was also outstanding. This extraordinary poster session was highlighted with the Monday evening "poster party" and culminated in the awarding of 37 poster prizes.OMCOS-13 was held as a single session conference in an impressive lecture theater and a large exhibition area in the center of Geneva at a superb lakefront location. It was a fitting venue for the firstclass science that was presented.Thirty-seven lecturers of OMCOS-13 present their chemistry in this issue of Pure and Applied Chemistry and provide a fine recollection of last summer's conference. The 14th edition of OMCOS will be held in Nara, Japan (2-6 August 2007) under the chairmanship of Prof. Koichiro Oshima.Alexandre AlexakisOMCOS-13 Co-chairE. Peter KündigOMCOS-13 Co-chair

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Silva, Eduarda, Artur Silva, and Djenisa Rocha. "Diels–Alder Reactions of 1,2-Dihydropyridines: An Efficient Tool for the Synthesis of Isoquinuclidines." Synthesis 50, no. 09 (2018): 1773–82. http://dx.doi.org/10.1055/s-0037-1609418.

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The Diels–Alder reaction of 1,2-dihydropyridines with different dienophiles is a well-established and straightforward method for the synthesis of isoquinuclidines. Nevertheless, the enantioselective preparation of isoquinuclidines using organocatalysts or organometallic catalysts is rather unexplored. This succinct review offers readers an overall perspective of the most important recent developments and concepts related to this topic.1 Introduction2 Asymmetric Diels–Alder Reaction of 1,2-Dihydropyridines2.1 Transition-Metal-Catalyzed Reactions2.2 Organocatalyzed Reactions3 Diels–Alder Reaction of 1,2-Dihydropyridines in the Synthesis of Biologically Valuable Compounds4 Conclusion

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Piccardi, Riccardo, Serge Turcaud, Erica Benedetti, and Laurent Micouin. "Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents." Synthesis 51, no. 01 (2018): 97–106. http://dx.doi.org/10.1055/s-0037-1610392.

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Organoaluminum derivatives are mostly appreciated for their Lewis acidity properties, but generally not considered as reagents of choice in synthetic transformations involving the creation of C–C bonds. Among these species, dimethylalkynylaluminum reagents represent a special class of compounds, with, in many cases, unique reactivity. This review summarizes the preparation and reactivity of these organometallic reagents with a focus on their synthetic potential.1 Introduction2 Preparation of Dimethylalkynylaluminum Reagents3 Reactivity of Dimethylalkynylaluminum Reagents3.1 Reactions with Csp3 Electrophiles3.2 Reactions with Csp2 Electrophiles4 Transition-Metal-Catalyzed Reactions4.1 Addition to α,β-Unsaturated Enones4.2 Coupling Reactions5 Triple Bond Reactivity6 Conclusion

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5

Arisawa, Mieko, and Masahiko Yamaguchi. "Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfur." Molecules 25, no. 16 (2020): 3595. http://dx.doi.org/10.3390/molecules25163595.

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Organosulfur compounds are widely used for the manufacture of drugs and materials, and their synthesis in general conventionally employs nucleophilic substitution reactions of thiolate anions formed from thiols and bases. To synthesize advanced functional organosulfur compounds, development of novel synthetic methods is an important task. We have been studying the synthesis of organosulfur compounds by transition-metal catalysis using disulfides and sulfur, which are easier to handle and less odiferous than thiols. In this article, we describe our development that rhodium complexes efficiently catalyze the cleavage of S-S bonds and transfer organothio groups to organic compounds, which provide diverse organosulfur compounds. The synthesis does not require use of bases or organometallic reagents; furthermore, it is reversible, involving chemical equilibria and interconversion reactions.

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6

Nicholas, Kenneth M., and Chandrasekhar Bandari. "Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides." Synthesis 53, no. 02 (2020): 267–78. http://dx.doi.org/10.1055/s-0040-1707269.

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AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amounts of low-valent transition-metal reagents to form the corresponding hydrocarbon dimers. More recently, the use of redox-active transition-metal catalysts together with a reductant has enhanced the practical applications and scope of the reductive coupling of alcohols. Inclusion of other reaction partners with alcohols such as unsaturated hydrocarbons and main-group organometallics has further expanded the diversity of carbon skeletons accessible and the potential for applications in chemical synthesis. Catalytic reductive coupling and cross-coupling reactions of epoxides are also highlighted. Mechanistic insights into the means of C–O activation and C–C bond formation, where available, are also highlighted.1 Introduction2 Stoichiometric Reductive Coupling of Alcohols3 Catalytic Reductive Coupling of Alcohols3.1 Heterogeneous Catalysis3.2 Homogeneous Catalysis4 Reductive Cross-Coupling of Alcohols4.1 Reductive Alkylation4.2 Reductive Addition to Olefins5 Epoxide Reductive Coupling Reactions6 Conclusions and Future Directions

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Diao, Tianning, Qiao Lin, and Gregory Dawson. "Experimental Electrochemical Potentials of Nickel Complexes." Synlett 32, no. 16 (2021): 1606–20. http://dx.doi.org/10.1055/s-0040-1719829.

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AbstractNickel-catalyzed cross-coupling and photoredox catalytic reactions has found widespread utilities in organic synthesis. Redox processes are key intermediate steps in many catalytic cycles. As a result, it is pertinent to measure and document the redox potentials of various nickel species as precatalysts, catalysts, and intermediates. The redox potentials of a transition-metal complex are governed by its oxidation state, ligand, and the solvent environment. This article tabulates experimentally measured redox potentials of nickel complexes supported on common ligands under various conditions. This review article serves as a versatile tool to help synthetic organic and organometallic chemists evaluate the feasibility and kinetics of redox events occurring at the nickel center, when designing catalytic reactions and preparing nickel complexes.1 Introduction1.1 Scope1.2 Measurement of Formal Redox Potentials1.3 Redox Potentials in Nonaqueous Solution2 Redox Potentials of Nickel Complexes2.1 Redox Potentials of (Phosphine)Ni Complexes2.2 Redox Potentials of (Nitrogen)Ni Complexes2.3 Redox Potentials of (NHC)Ni Complexes

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Manners, Ian. "Article." Canadian Journal of Chemistry 76, no. 4 (1998): 371–81. http://dx.doi.org/10.1139/v98-054.

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Ring-opening polymerization (ROP) of strained ring-tilted metallocenophanes can be achieved thermally, via anionic or cationic initiation, or by the use of transition-metal catalysts and provides access to a wide range of high molecular weight (Mw = 105-106, Mn > 105) poly(metallocenes). These materials possess a variety of interesting properties and many are very easy to prepare. This article provides an overview of our work, giving background to and an account of the initial discovery, and discusses work on the synthesis and properties of new poly(metallocenes) and related materials with particular emphasis on recent research directions.Key words: metallocene, ring-opening polymerization, ferrocenophane, organometallic polymer.

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9

Butenschön, Holger. "Transition Metal Arene π-Complexes in Organic Synthesis and Catalysis. (Series: Topics in Organometallic Chemistry, Vol. 7.). Edited by E. Peter Kündig." Angewandte Chemie International Edition 44, № 11 (2005): 1591–92. http://dx.doi.org/10.1002/anie.200485231.

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Fui, Choong Jian, Mohd Sani Sarjadi, Shaheen M. Sarkar, and Md Lutfor Rahman. "Recent Advancement of Ullmann Condensation Coupling Reaction in the Formation of Aryl-Oxygen (C-O) Bonding by Copper-Mediated Catalyst." Catalysts 10, no. 10 (2020): 1103. http://dx.doi.org/10.3390/catal10101103.

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Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and synthetic pharmaceuticals but also widely found in many pesticides, polymers, and ligands. Copper catalyst has received great attention owing to the low toxicity and low cost. However, traditional Ullmann-type couplings suffer from limited substrate scopes and harsh reaction conditions. The introduction of homogeneous copper catalyst with presence of bidentate ligands over the past two decades has totally changed this situation as these ligands enable the reaction promoted in mild condition. The reaction scope has also been greatly expanded, rendering this copper-based cross-coupling attractive for both academia and industry. In this review, we will highlight the latest progress in the development of useful homogeneous copper catalyst with presence of ligand and heterogeneous copper catalyst in Ullmann type C-O cross-coupling reaction. Additionally, the application of Ullmann type C-O cross coupling reaction will be discussed.

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Butenschön, Holger. "Transition Metal Arene π-Complexes in Organic Synthesis and Catalysis. Band 7 der Reihe Topics in Organometallic Chemistry. Herausgegeben von E. Peter Kündig." Angewandte Chemie 117, № 11 (2005): 1618–19. http://dx.doi.org/10.1002/ange.200485231.

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12

Azizollahi, Hamid, and José-Antonio García-López. "Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage." Molecules 25, no. 24 (2020): 5900. http://dx.doi.org/10.3390/molecules25245900.

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The functionalization of C–H bonds has become a major thread of research in organic synthesis that can be assessed from different angles, for instance depending on the type of catalyst employed or the overall transformation that is carried out. This review compiles recent progress in synthetic methodology that merges the functionalization of C–H bonds along with the cleavage of C–C bonds, either in intra- or intermolecular fashion. The manuscript is organized in two main sections according to the type of substrate in which the cleavage of the C–C bond takes place, basically attending to the scission of strained or unstrained C–C bonds. Furthermore, the related research works have been grouped on the basis of the mechanistic aspects of the different transformations that are carried out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates are involved; (b) processes occurring via radical intermediates generated through the use of radical initiators or photochemically; and (c) reactions that are catalyzed or mediated by suitable Lewis or Brønsted acid or bases, where molecular rearrangements take place. Thus, throughout the review a wide range of synthetic approaches show that the combination of C–H and C–C cleavage in single synthetic operations can serve as a platform to achieve complex molecular skeletons in a straightforward manner, among them interesting carbo- and heterocyclic scaffolds.

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13

Schmalz, Hans-Günther. "Book Review: Transition Metal Organometallics for Organic Synthesis. By F. J. McQuillin, D. G. Parker and G. R. Stephenson." Angewandte Chemie International Edition in English 32, no. 2 (1993): 307–8. http://dx.doi.org/10.1002/anie.199303072.

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14

Gafurov, Zufar N., Artyom O. Kantyukov, Alexey A. Kagilev, et al. "Recent Advances in Chemistry of Unsymmetrical Phosphorus-Based Pincer Nickel Complexes: From Design to Catalytic Applications." Molecules 26, no. 13 (2021): 4063. http://dx.doi.org/10.3390/molecules26134063.

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Pincer complexes play an important role in organometallic chemistry; in particular, their use as homogeneous catalysts for organic transformations has increased dramatically in recent years. The high catalytic activity of such bis-cyclometallic complexes is associated with the easy tunability of their properties. Moreover, the phosphorus-based unsymmetrical pincers showed higher catalytic activity than the corresponding symmetrical analogues in several catalytic reactions. However, in modern literature, an increasing interest in the development of catalysts based on non-precious metals is observed. For example, nickel, which is an affordable and sustainable analogue of platinum and palladium, known for its low toxicity, has attracted increasing attention in the catalytic chemistry of transition metals in recent years. Thus, this mini-review is devoted to the recent advances in the chemistry of unsymmetrical phosphorus-based pincer nickel complexes, including the ligand design, the synthesis of nickel complexes and their catalytic applications.

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15

Woźniak, Krzysztof. "Preface." Pure and Applied Chemistry 79, no. 6 (2007): iv. http://dx.doi.org/10.1351/pac20077906iv.

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The 18th International Conference on Physical Organic Chemistry (ICPOC-18) took place at the Gromada Hotel in Warsaw, Poland on 20-25 August 2006 under the local auspices of Warsaw University and the Polish Chemical Society. It was organized by a local Organizing Committee from the Department of Chemistry of Warsaw University led by Prof. Tadeusz M. Krygowski.Although physical organic chemistry began in the 1930s and at the beginning was concerned mostly with the mechanisms and kinetics of organic reactions and their dependence on structural and medium effects, a great extension of the field toward bioorganic, organic, organometallic, theoretical, catalytic, supramolecular, and photochemistry has been observed for decades now. Representative topics for modern physical organic chemistry include: reaction mechanisms; reactive intermediates; bioprocesses; novel structures; reactivity relationships; solvent, substituent, isotope, and solid-state effects; long-lived charges; sextet or open-shell species; magnetic, nonlinear optical, and conducting molecules; and molecular recognition. Contributions from all of these fields were presented.About 220 researchers, representing 31 countries, participated in the conference. The following eight plenary lectures were presented:R. Huber (Nobel laureate, Germany): "Molecular machines in biology"A. Yonath (Israel): "The spectacular ribosomal architecture: Nascent proteins voyage towards folding via antibiotics binding-pockets"P. Coppens (USA): "Time-resolved diffraction studies of molecular excited states and beyond"K. S. Kim (South Korea): "De novo design based on nano-recognition: Functional molecules/materials and nanosensors/nanodevices"I. P. Beletskaya (Russia): "Mechanistic aspects and synthetic application of carbon-carbon and carbon-heteroatom bonds formation in substitution and addition reactions catalyzed by transition-metal complexes"S. Fukuzumi (Japan): "New development of electron-transfer catalytic systems"D. Braga (Italy): "Making crystals from crystals: A green route to crystal engineering and polymorphism"L. Latos-Grażyński (Poland): "Carbaporphyrinoids: Exploring metal ion-arene interaction in a macrocyclic environment"Additionally, 17 invited talks and, during two parallel sessions, 51 oral communications were presented. There were more than 100 poster presentations.I am pleased to introduce a representative selection of outstanding papers based on plenary and invited lectures delivered at ICPOC-18. In addition to the contributions mentioned above, this volume contains: a discussion of modern understanding of aromaticity (P. Fowler, UK); fascinating studies of new mechanisms focused on reactive intermediates (R. Moss, USA); interpretation of acidity, basicity, and hydride affinity by the trichotomy paradigm (Z. Maksić, Croatia); a quantum approach to proton transfer across hydrogen bond (F. Fillaux, France); a discussion of self-assembly of nickel(II) pseudorotaxene nanostructures on Au surface (R. Bilewicz, Poland); a discussion of synthesis and properties of macrocyclic receptors for anions (J. Jurczak, Poland); a description of novel organic-inorganic frameworks (J. Klinowski, UK); an application of microemulsions as microreactors (J. R. Leis, Spain); a discussion of silicon rehybridization and molecular rearrangements in hypercoordinate silicon dichelates (D. Kost, Israel); and a description of solvation in pure and mixed solvents (O. El Seoud, Brazil). All of these papers exemplify the broad range and diversity of interests of the participants and characterize the present and future challenges in physical organic chemistry.The social program of the conference included: a welcome reception; a Chopin music concert organized in cooperation with the Frederic Chopin Society; conference excursions, including Warsaw Old Town and Żelazowa Wola, the house where Chopin was born; the Warsaw Uprising (1944) Museum and the Heroes of Ghetto Memorial; and folk music dances during the conference dinner.Because ICPOC-18 was attended by quite a number of young chemists from all over the world, it can be expected that the next conference in this series, ICPOC-19, which will be held in July 2008 and is being organized by Profs. J. Ramon Leis from the University of Santiago de Compostela and A. Santaballa from the University of A Coruna (Spain), will not only reflect recent developments and the rich potential of physical organic chemistry, but will also demonstrate the aspirations of younger generations of scientists in this field.Krzysztof WoźniakConference Editor

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Periana, Roy A. "Transition Metal Arene π-Complexes in Organic Synthesis and Catalysis. Topics in Organometallic Chemistry, 7 Edited by E. Peter Kündig (University of Geneva). Springer-Verlag: Berlin, Heidelberg, New York. 2004. viii + 232 pp. $269.00. ISBN 3-540-01604-X." Journal of the American Chemical Society 127, № 5 (2005): 1589. http://dx.doi.org/10.1021/ja040984i.

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Lee, Daesung, and Sangho Park. "Transition-Metal-Based Synthesis of Dendralenes." Synthesis 2007, no. 15 (2007): 2313–16. http://dx.doi.org/10.1055/s-2007-966069.

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18

Cornella, Josep, and Matthew O’Neill. "Retaining Alkyl Nucleophile Regiofidelity in Transition-Metal-Mediated Cross-Couplings to Aryl Electrophiles." Synthesis 50, no. 20 (2018): 3974–96. http://dx.doi.org/10.1055/s-0037-1609941.

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While the advent of transition-metal catalysis has undoubtedly transformed synthetic chemistry, problems persist with the introduction of secondary and tertiary alkyl nucleophiles into C(sp2) aryl electrophiles. Complications arise from the delicate organometallic intermediates typically invoked by such processes, from which competition between the desired reductive elimination event and the deleterious β-H elimination pathways can lead to undesired isomerization of the incoming nucleophile. Several methods have integrated distinct combinations of metal, ligand, nucleophile, and electrophile to provide solutions to this problem. Despite substantial progress, refinements to current protocols will facilitate the realization of complement reactivity and improved functional group tolerance. These issues have become more pronounced in the context of green chemistry and sustainable catalysis, as well as by the current necessity to develop robust, reliable cross-couplings beyond less explored C(sp2)–C(sp2) constructs. Indeed, the methods discussed herein and the elaborations thereof enable an ‘unlocking’ of accessible topologically enriched chemical space, which is envisioned to influence various domains of application.1 Introduction2 Mechanistic Considerations3 Magnesium Nucleophiles4 Zinc Nucleophiles5 Boron Nucleophiles6 Other Nucleophiles7 Tertiary Nucleophiles8 Reductive Cross-Coupling with in situ Organometallic Formation9 Conclusion

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Shiri, Morteza, Noushin Farajinia-Lehi, Parvin Salehi, and Zahra Tanbakouchian. "Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry." Synthesis 52, no. 21 (2020): 3162–88. http://dx.doi.org/10.1055/s-0040-1707357.

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AbstractThe synthesis of amides is a substantial research area in organic chemistry because of their ubiquitous presence in natural products and bioactive molecules. The use of easily accessible isocyanides as amidoyl (carbamoyl) synthons in cross-coupling reactions using transition metal and inner transition metöal catalysts is a current trend in this area. Isocyanides, owing to their coordination ability as a ligand and inherent electronic properties for reactions with various partners, have expanded the potential application of these transformations for the preparation of novel synthetic molecules and pharmaceutical candidates. This review gives an overview of the achievements in isocyanide-based transition metal and inner transition metal catalyzed amide formation and discusses highlights of the proposed distinct mechanisms.1 Introduction2 Synthesis of Arenecarboxamides3 Synthesis of Alkanamides4 Synthesis of Cyclic Amides5 Formation of Alkynamides6 Formation of Acrylamide-like Molecules7 Formation of Ureas and Carbamates8 Conclusion

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Roh, Sang Weon, Kyoungmin Choi, and Chulbom Lee. "Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis." Chemical Reviews 119, no. 6 (2019): 4293–356. http://dx.doi.org/10.1021/acs.chemrev.8b00568.

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Mialane, P., C. Mellot-Draznieks, P. Gairola, et al. "Heterogenisation of polyoxometalates and other metal-based complexes in metal–organic frameworks: from synthesis to characterisation and applications in catalysis." Chemical Society Reviews 50, no. 10 (2021): 6152–220. http://dx.doi.org/10.1039/d0cs00323a.

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Tomboc, Gracita M., Yeji Park, Kwangyeol Lee, and Kyoungsuk Jin. "Directing transition metal-based oxygen-functionalization catalysis." Chemical Science 12, no. 26 (2021): 8967–95. http://dx.doi.org/10.1039/d1sc01272j.

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Beletskaya, Irina P., and Andrei V. Cheprakov. "Transition Metal Complex Catalysis in Fine Organic Synthesis. A Personal Account." Collection of Czechoslovak Chemical Communications 68, no. 10 (2003): 1904–13. http://dx.doi.org/10.1135/cccc20031904.

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The development of catalytic systems for palladium catalyzed C-C and C-heteroatom bond formation is overviewed. Attention is focused on the issues relevant for environmental and technological safety of the processes: high catalytic efficiency, reactions in the absence of expensive non-recoverable phosphine ligands, the use of water and aqueous media, atom efficient transformations, etc.

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Johnson, Erin R., and Axel D. Becke. "Tests of an exact-exchange-based density-functional theory on transition-metal complexes." Canadian Journal of Chemistry 87, no. 10 (2009): 1369–73. http://dx.doi.org/10.1139/v09-102.

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We have compiled a benchmark set of mean ligand-removal enthalpies for 32 transition-metal complexes of relevance in organometallic and catalysis chemistry. Our recent exact-exchange-based density-functional model, DF07 ( J. Chem. Phys. 2007, 127 (12), 124108 ), is assessed on this benchmark set along with other representative GGA, meta-GGA, and hybrid functionals. DF07 performs remarkably well, despite its exact-exchange foundation, indicating that it properly describes nondynamical correlation in transition-metal–ligand bonds.

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Maiden, T. M. M., and J. P. A. Harrity. "Recent developments in transition metal catalysis for quinazolinone synthesis." Organic & Biomolecular Chemistry 14, no. 34 (2016): 8014–25. http://dx.doi.org/10.1039/c6ob01402j.

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This review describes recent developments in the employment of catalytic methods for the synthesis of quinazolinones, an important class of heterocycles that are prevalent in a variety of important bio-active scaffolds.

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Willis, Michael C. "Modern applications of transition metal catalysis in heterocycle synthesis." Tetrahedron 65, no. 44 (2009): 8907. http://dx.doi.org/10.1016/j.tet.2009.08.065.

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Diao, Tianning, and David Anthony. "Asymmetric Reductive Dicarbofunctionalization of Alkenes via Nickel Catalysis." Synlett 31, no. 15 (2020): 1443–47. http://dx.doi.org/10.1055/s-0040-1707900.

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Alkenes are an appealing functional group that can be transformed into a variety of structures. Transition-metal catalyzed dicarbofunctionalization of alkenes can efficiently afford products with complex substitution patterns from simple substrates. Under reductive conditions, this transformation can be achieved while avoiding stoichiometric organometallic reagents. Asymmetric difunctionalization of alkenes has been underdeveloped, in spite of its potential synthetic utility. Herein, we present a summary of our efforts to control enantioselectivity for alkene diarylation with a nickel catalyst. This reaction is useful for preparing triarylethanes. The selectivity is enhanced by an N-oxyl radical additive.

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Ganley, Jacob M., and David L. Waller. "Synthesis of Furo[2,3-c]pyridazines via Tandem Transition-Metal Catalysis." Journal of Organic Chemistry 82, no. 23 (2017): 12740–45. http://dx.doi.org/10.1021/acs.joc.7b01819.

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Kočovský, Pavel, Andrei V. Malkov, Štěpán Vyskočil, and Guy C. Lloyd-Jones. "Transition metal catalysis in organic synthesis: reflections, chirality and new vistas." Pure and Applied Chemistry 71, no. 8 (1999): 1425–33. http://dx.doi.org/10.1351/pac199971081425.

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Knolker, Hans-Joachim. "Transition Metal Complexes in Organic Synthesis, Part 70&#. Synthesis of Biologically Active Carbazole Alkaloids Using Organometallic Chemistry." Current Organic Synthesis 1, no. 4 (2004): 309–31. http://dx.doi.org/10.2174/1570179043366594.

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Prier, Christopher K., Danica A. Rankic, and David W. C. MacMillan. "Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis." Chemical Reviews 113, no. 7 (2013): 5322–63. http://dx.doi.org/10.1021/cr300503r.

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Ogasawara, Masamichi, and Susumu Watanabe. "Transition-Metal-Catalyzed Enantioselective Synthesis of Compounds with Non-Centrochirality." Synthesis 2009, no. 11 (2009): 1761–85. http://dx.doi.org/10.1055/s-0029-1216818.

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Ogasawara, Masamichi, and Susumu Watanabe. "Transition-Metal-Catalyzed Enantioselective Synthesis of Compounds with Non-Centrochirality." Synthesis 2009, no. 18 (2009): 3177–78. http://dx.doi.org/10.1055/s-0029-1216988.

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34

Chauhan, S., Pratibha Kumari, and Shweta Agarwal. "Efficient Synthesis of Transition-Metal Phthalocyanines in Functional Ionic Liquids." Synthesis 2007, no. 23 (2007): 3713–21. http://dx.doi.org/10.1055/s-2007-990879.

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35

Feng, Lei, Chen Ma, Fangdong Hu, Xin Zhao, and Yanqiu Li. "Regioselective Synthesis of Phenoxathiin Derivatives under Transition-Metal-Free Conditions." Synthesis 45, no. 07 (2013): 966–70. http://dx.doi.org/10.1055/s-0032-1316863.

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36

Davis, Anthony, D. Walker, and Joshua Howgego. "Synthesis of Regioselectively Functionalized Pyrenes via Transition-Metal-Catalyzed Electrocyclization." Synthesis 2010, no. 21 (2010): 3686–92. http://dx.doi.org/10.1055/s-0030-1258238.

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37

Nyamori, Vincent O., Sabelo D. Mhlanga, and Neil J. Coville. "The use of organometallic transition metal complexes in the synthesis of shaped carbon nanomaterials." Journal of Organometallic Chemistry 693, no. 13 (2008): 2205–22. http://dx.doi.org/10.1016/j.jorganchem.2008.04.003.

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38

Arrington, Kenneth, Gregg A. Barcan, Nicholas A. Calandra, et al. "Convergent Synthesis of the NS5B Inhibitor GSK8175 Enabled by Transition Metal Catalysis." Journal of Organic Chemistry 84, no. 8 (2018): 4680–94. http://dx.doi.org/10.1021/acs.joc.8b02269.

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39

Genêt, Jean-Pierre, Sylvain Darses, and Véronique Michelet. "Organometallic catalysts in synthetic organic chemistry: From reactions in aqueous media to gold catalysis." Pure and Applied Chemistry 80, no. 5 (2008): 831–44. http://dx.doi.org/10.1351/pac200880050831.

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Water has attracted significant attention as an alternative solvent for transition-metal-catalyzed reactions. The use of water as solvent allows simplified procedures for separation of the catalyst from the products and recycling of the catalyst. Water is an inexpensive reagent for the formation of oxygen-containing products such as alcohols. The use of water as a medium for promoting organometallic and organic reactions is also of great potential. This chapter will focus on old and recent developments in the design and applications of some catalytic reactions using aqueous-phase Pd, Rh, Pt, and Au complexes.

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Vaitla, Janakiram, and Annette Bayer. "Sulfoxonium Ylide Derived Metal Carbenoids in Organic Synthesis." Synthesis 51, no. 03 (2018): 612–28. http://dx.doi.org/10.1055/s-0037-1610328.

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As pioneered by Corey and Chaykovsky, sulfoxonium ylides have had widespread application in organic synthesis for more than a half century. In most of the reactions, sulfoxonium ylides were used to react with electrophiles. Under suitable reaction conditions these ylides can generate metal carbenoids and react with nucleophiles. By combining the typical reactivity of sulfoxonium ylides with transition-metal catalysis, a growing number of investigations have expanded their application in organic synthesis. This review provides an update on the preparation of sulfoxonium ylides and their applications in carbenoid transfer reactions.1 Introduction2 Preparation of Sulfoxonium Ylides3 Investigation for Carbenoid Formation from Sulfoxonium Ylide 4 X–H (X = N, O, S, C) Functionalization Reactions5 Polymerizaton of Carbenoids Generated from Sulfoxonium Ylides6 Conclusion and Perspective

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Kumar, N., Dennis G. Tuck, and Katherine D. Watson. "The direct electrochemical synthesis of some transition metal carboxylates." Canadian Journal of Chemistry 65, no. 4 (1987): 740–43. http://dx.doi.org/10.1139/v87-125.

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The transition metal carboxylates M(O2CR)n (M = Cr, R = C2H5, C6H5, n = 3; M = Mn, Fe, Ni, R = CH3, C2H5, C6H5, n-C7H15, n = 2, not all combinations) have been prepared by oxidising suitable metal anodes electrochemically in solutions of RCOOH in acetonitrile. With Co and Cu, a wide range of carboxylic acids (R = C2H5, c-C3H5, c-C5H9, C6H5, n-C4H9, n-C7H15, 2-ethylhexanoic, oleic, linoleic) has been used successfully to give M(O2CR)2. The advantages of the method are discussed. The preparation of Cu(O2CR)2 involves the prior formation of CuO2CR at the anode, followed by oxidation by the solvent.

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Hsieh, Jen-Chieh, and Haw-Lih Su. "Synthesis of N-Heterocycles via Transition-Metal-Catalyzed Tandem Addition/Cyclization of a Nitrile." Synthesis 52, no. 06 (2020): 819–33. http://dx.doi.org/10.1055/s-0039-1691561.

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The diverse methodologies to synthesize N-heterocycles through transition-metal-catalyzed cascade addition/cyclization of a nitrile are discussed in this review. Aspects relating to three types of transition-metal-catalyzed addition of a nitrile with subsequent cyclization include (1) a transition-metal acting as a Lewis acid to accelerate the nucleophilic addition of a nitrile, (2) the late-transition-metal-catalyzed 1,2-insertion of a nitrile, and (3) an in situ generated radical by transition-metal catalysis to implement a radical addition/cyclization tandem reaction. Applications for the synthesis of natural alkaloids, their derivatives, and some bioactive compounds are also summarized herein.1 Introduction2 Nucleophilic Addition of a Nitrile Accelerated by a Lewis Acid2.1 Late-Transition-Metal Catalysis2.2 Early-Transition-Metal Catalysis2.3 Lanthanide-Metal Catalysis2.4 Cyclization from N-Arylnitriliums3 Transition-Metal-Catalyzed Insertion of a Nitrile4 Transition-Metal-Catalyzed Radical Addition of a Nitrile5 Conclusions

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Baird, Michael C. "Catalysis by organotransition metal compounds: Synergism between the pure and the applied1." Canadian Journal of Chemistry 81, no. 4 (2003): 330–37. http://dx.doi.org/10.1139/v03-065.

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The modern era of transition-metal-catalyzed polymerization of alkenes began with the Nobel Prize winning work of Ziegler and Natta in the 1950s, but the field has exploded since the mid-1980s and anticipated applications of organometallic catalysts are being spectacularly realized. Our research in metal-catalyzed alkene polymerization began about ten years ago with an investigation of the catalytic applications of half-sandwich complexes of the Group 4 metals, and this lecture will describe our efforts to find both better initiators to make known commercial polymers and new initiators to make novel polymeric materials. Good luck, bad luck, blind alleys, and serendipity have all played key roles in our research, resulting ultimately in a very satisfying convergence of the motives for pure, and the needs of applied, research.Key words: alkene, polymerization, Ziegler, catalysis, carbocationic, titanium.

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44

Kurandina, Daria, Padon Chuentragool, and Vladimir Gevorgyan. "Transition-Metal-Catalyzed Alkyl Heck-Type Reactions." Synthesis 51, no. 05 (2019): 985–1005. http://dx.doi.org/10.1055/s-0037-1611659.

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The Heck reaction is one of the most reliable and useful strategies for the construction of C–C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018.1 Introduction2 Pd-Catalyzed Heck-Type Reactions2.1 Benzylic Electrophiles2.2 α-Carbonyl Alkyl Halides2.3 Fluoroalkyl Halides2.4 α-Functionalized Alkyl Halides2.5 Unactivated Alkyl Electrophiles3 Ni-Catalyzed Heck-Type Reactions3.1 Benzylic Electrophiles3.2 α-Carbonyl Alkyl Halides3.3 Unactivated Alkyl Halides4 Co-Catalyzed Heck-Type Reactions5 Cu-Catalyzed Heck-Type Reactions6 Other Metals in Heck-Type Reactions7 Conclusion

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van Esseveldt, Bart C J., Floris L van Delft, Jan M M. Smits, René de Gelder, Hans E Schoemaker, and Floris P J. T. Rutjes. "Transition Metal-Catalyzed Synthesis of Novel Biologically Relevant Tryptophan Analogues." Advanced Synthesis & Catalysis 346, no. 7 (2004): 823–34. http://dx.doi.org/10.1002/adsc.200404012.

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46

Arisawa, Mieko. "Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage." Synthesis 52, no. 19 (2020): 2795–806. http://dx.doi.org/10.1055/s-0040-1707890.

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Organophosphorus compounds are used as drugs, pesticides, detergents, food additives, flame retardants, synthetic reagents, and catalysts, and their efficient synthesis is an important task in organic synthesis. To synthesize novel functional organophosphorus compounds, transition-metal-catalyzed methods have been developed, which were previously considered difficult because of the strong bonding that occurs between transition metals and phosphorus. Addition reactions of triphenylphosphine and sulfonic acids to unsaturated compounds in the presence of a rhodium or palladium catalyst lead to phosphonium salts, in direct contrast to the conventional synthesis involving substitution reactions of organohalogen compounds. Rhodium and palladium complexes catalyze the cleavage of P–P bonds in diphosphines and polyphosphines and can transfer organophosphorus groups to various organic compounds. Subsequent substitution and addition reactions proceed effectively, without using a base, to provide various novel organophosphorus compounds.1 Introduction2 Transition-Metal-Catalyzed Synthesis of Phosphonium Salts by Addition Reactions of Triphenylphosphine and Sulfonic Acids3 Rhodium-Catalyzed P–P Bond Cleavage and Exchange Reactions4 Transition-Metal-Catalyzed Substitution Reactions Using Diphosphines4.1 Reactions Involving Substitution of a Phosphorus Group by P–P Bond Cleavage4.2 Related Substitution Reactions of Organophosphorus Compounds4.3 Substitution Reactions of Acid Fluorides Involving P–P Bond Cleavage of Diphosphines5 Rhodium-Catalyzed P–P Bond Cleavage and Addition Reactions6 Rhodium-Catalyzed P–P Bond Cleavage and Insertion Reactions Using Polyphosphines7 Conclusions

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Wachter, Joachim. "Synthesis, Structure and Reactivity of Sulfur-Rich Cyclopentadienyl-Transition Metal Complexes: Sulfur Chemistry from an Organometallic Point of View." Angewandte Chemie International Edition in English 28, no. 12 (1989): 1613–26. http://dx.doi.org/10.1002/anie.198916131.

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48

Kräutler, Bernhard, Florian J. Widner, Christoph Kieninger, et al. "Synthesis, Spectral Characterization and Crystal Structure of Chlororhodibalamin: A Synthesis Platform for Rhodium Analogues of Vitamin B12 and for Rh-Based Antivitamins B12." Synthesis 53, no. 02 (2020): 332–37. http://dx.doi.org/10.1055/s-0040-1707288.

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AbstractChlororhodibalamin (ClRhbl), a rhodium analogue of vitamin B12 (cyanocobalamin), was prepared in 84% yield by metalation of the metal-free B12 ligand hydrogenobalamin using the RhI-complex [Rh(CO)2Cl]2. ClRhbl was identified and characterized by UV/Vis, circular dichroism, high-resolution mass and heteronuclear NMR spectra. The RhIII-corrin ClRhbl features the ‘base-on’ architecture of vitamin B12. X-ray analysis of single crystals of ClRhbl have revealed its detailed 3D-geometry and close structural similarity to the CoIII-analogue chlorocobalamin (ClCbl). ClRhbl is a versatile starting material for the preparation of other rhodibalamins, among them the organometallic derivatives adenosylrhodibalamin and methylrhodibalamin, the Rh analogues of the important coenzyme and cofactor forms of B12, adenosylcobalamin and methylcobalamin.

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Lee, Donald G., and Ligaya N. Congson. "Kinetics and mechanism of the oxidation of alcohols by ruthenate and perruthenate ions." Canadian Journal of Chemistry 68, no. 10 (1990): 1774–79. http://dx.doi.org/10.1139/v90-276.

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In addition to being important synthetic reagents, ruthenate and perruthenate are of interest because they are representative of a number of high valent transition metal ions that can be used as oxidants in organic chemistry. In their reactions with alcohols both ions exhibit several striking similarities — concave Hammett plots, primary deuterium isotope effects, small enthalpies of activation, and large negative entropies of activation. The most likely explanation of the concave upward Hammett plots is the involvement of free radical-like transition states that could be formed by the decomposition of organometallic intermediates. Keywords: oxidation, ruthenate, perruthenate, alcohols, mandelic acid.

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Brown, Michael J., Guy J. Clarkson, Graham G. Inglis, and Michael Shipman. "Synthesis and Functionalization of 3-Alkylidene-1,2-diazetidines Using Transition Metal Catalysis." Organic Letters 13, no. 7 (2011): 1686–89. http://dx.doi.org/10.1021/ol200193n.

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