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Journal articles on the topic 'Carbonyl compounds. Organometallic compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Vizer, S. A., and K. B. Yerzhanov. "Heterocycles Synthesis at Carbonylation of Acetylenic Compounds." Eurasian Chemico-Technological Journal 5, no. 2 (2016): 145. http://dx.doi.org/10.18321/ectj294.

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The carbonylation of unsaturated hydrocarbons, alcohols, organic halides and other substrates catalyzed by transition metals, salts of transition metals and organometallic complexes is a wide used synthesis method of new carbonyl, carboxyl and alkoxy carbonyl containing compounds including creation or modificationt of heterocycles. The data about synthesis of heterocycles at carbonylation of acetylenic compounds have been appeared at last 20 years and are demonstrated in our review. Introduction of carbon monoxide in the catalytic reactions of acetylenic compounds permits to obtain in oneput process the diverse heterocycles, having carbonyl, carboxyl or alkoxycarbonyl substitutes or containing these fragments inside of heterocycles.

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2

Mendes-Burak, Jorge, Behnaz Ghaffari та Christophe Copéret. "Selective hydrogenation of α,β-unsaturated carbonyl compounds on silica-supported copper nanoparticles". Chemical Communications 55, № 2 (2019): 179–81. http://dx.doi.org/10.1039/c8cc08457b.

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Silica-supported copper nanoparticles prepared via surface organometallic chemistry are highly efficient for the selective hydrogenation of various α,β-unsaturated carbonyl compounds yielding the corresponding saturated esters, ketones, and aldehydes in the absence of additives.

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3

Pignon, Antoine, Erwan Le Gall, and Thierry Martens. "A new manganese-mediated, cobalt-catalyzed three-component synthesis of (diarylmethyl)sulfonamides." Beilstein Journal of Organic Chemistry 10 (February 17, 2014): 425–31. http://dx.doi.org/10.3762/bjoc.10.39.

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The synthesis of (diarylmethyl)sulfonamides and related compounds by a new manganese-mediated, cobalt-catalyzed three-component reaction between sulfonamides, carbonyl compounds and organic bromides is described. This organometallic Mannich-like process allows the formation of the coupling products within minutes at room temperature. A possible mechanism, emphasizing the crucial role of manganese is proposed.

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4

Pedro, Filipe M., Ana M. Santos, Walter Baratta, and Fritz E. Kühn. "Organometallic Ruthenium Complexes: Application in the Olefination of Carbonyl Compounds." Organometallics 26, no. 2 (2007): 302–9. http://dx.doi.org/10.1021/om060508w.

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5

Collins, Scott, Yaping Hong, Gordon J. Hoover, and Jennifer R. Veit. "Additions of alkyllathanum triflates to carbonyl compounds: reactive organometallic nucleophiles." Journal of Organic Chemistry 55, no. 11 (1990): 3565–68. http://dx.doi.org/10.1021/jo00298a035.

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6

Jackson, WR, ID Rae, and MG Wong. "The Stereochemistry of Organometallic Compounds .XXVII. Nucleophilic and Electrophilic Substitution-Reactions of Conformationally Restricted Arenechromium Compounds." Australian Journal of Chemistry 39, no. 2 (1986): 303. http://dx.doi.org/10.1071/ch9860303.

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The regioselectivity of reaction of tricarbonyl (1,1- dimethylindane )chromium with selected electrophiles and nucleophiles has been shown to be influenced by the preferred conformation of the tricarbonylchromium group. Nucleophiles preferentially react at carbon atoms eclipsed by a chromium-carbonyl bond and electrophiles at carbon atoms in staggered positions. When similar reactions were attempted with some chelated arenechromium dicarbonyl phosphorus compounds only low yields of substitution products were obtained.

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7

Decostanzi, Mélanie, Jean-Marc Campagne, and Eric Leclerc. "Low-Temperature Intermolecular Addition of RCF2Li Compounds to Various Carbonyl Electrophiles for a Practical Synthesis of CF2-Containing Building Blocks." Synthesis 48, no. 19 (2016): 3420–28. http://dx.doi.org/10.1055/s-0035-1562786.

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The addition of various RCF2Li compounds to a wide range of carbonyl electrophiles (aldehydes, ketones, acylsilanes, esters, and lactones) is reported. The reaction proceeds at very low temperature under Barbier conditions through a Br/Li exchange from the corresponding RCF2Br compounds. In contrast with existing methods that use more stable, but less reactive, organometallic species, there is efficient addition to esters, lactones and poorly reactive ketones.

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8

Blay, Gonzalo, José Pedro, and Amparo Sanz-Marco. "Conjugate Alkynylation of Electrophilic Double Bonds. From Regioselectivity to Enantioselectivity." Synthesis 50, no. 17 (2018): 3281–306. http://dx.doi.org/10.1055/s-0037-1610182.

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This review surveys the historical efforts addressed toward the development of the conjugate alkynylation reaction. The regio- and enantioselective conjugate alkynylation of electron-deficient double bonds, most commonly unsaturated carbonyl compounds, has been an elusive reaction for a long time. Intensive research during the last decades has resulted in the identification of a number of effective reagents and catalysts to perform this reaction. Non-stereoselective conjugate alkynylation of unsaturated carbonyl compounds was first achieved by using preformed alkynyl organometallics and later with terminal alkynes under catalytic conditions. These methods paved the way for the development of enantioselective procedures. After initial methods requiring stoichiometric amounts of chiral material, the findings by Corey on Ni-catalyzed addition of alkynylalanes and, particularly, by Carreira on Cu-catalyzed addition of terminal alkynes boosted the research on the development other asymmetric procedures catalyzed by Cu, Zn, Rh, Co, Ru and Pd complexes. The alkynylation of electrophilic alkenes conjugated with groups other than carbonyl and the alkynylation of extended conjugated systems are also discussed in the last part of this review.1 Introduction2 Non-Stereoselective Conjugate Alkynylation of α,β-Unsaturated Carbonyl Compounds3 Enantioselective Conjugate Alkynylation of α,β-Unsaturated Carbonyl Compounds4 Non-Stereoselective and Enantioselective Alkynylation of Other Electrophilic Alkenes5 γ-Alkynylation of α,β-Unsaturated Amides and δ-Alkynylation of Electrophilic Dienes6 Alternative Enantioselective Procedures7 Conclusion and Outlook

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9

Kauffmann, Thomas, Jan Jordan, and Karl-Uwe Voss. "Methylating Reductive Dimerization of Aromatic Carbonyl Compounds, a Novel Organometallic Reaction." Angewandte Chemie International Edition in English 30, no. 9 (1991): 1138–39. http://dx.doi.org/10.1002/anie.199111381.

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10

Lombardo, Marco, Sebastiano Licciulli, and C. Trombini. "3-Halopropenyl esters as precursors of a new class of oxygen-substituted allylic organometallic compounds: Applications in organic synthesis." Pure and Applied Chemistry 76, no. 3 (2004): 657–69. http://dx.doi.org/10.1351/pac200476030657.

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3-halopropenyl esters, readily prepared by the addition of acyl halides to acrolein, react with zinc, indium, and chromium(II), thus opening a route to a new class of oxygen-substituted allylic organometallic compounds. Indium and zinc reagents smoothly add to carbonyl compounds, affording alk-1-en-3,4-diol derivatives in a variety of synthetic procedures which include typical Grignard stepwise conditions as well as Barbier one-pot protocols. Using zinc and indium in water or aprotic solvents, simple diastereoselectivity was found to depend on the nature of the carbonyl compound; conjugated aldehydes favor formation of syn-adducts while unconjugated aldehydes favor anti-adducts. Moving to chromium, a reversal of regioselectivity was observed in favor of (Z)-4-hydroxy-enolacetates, flexible protected forms of homoaldols. Chromium complexes are generated in a catalytic cycle based on the combined use of the redox Mn(0)/Cr(III) couple and of TMSCl. When the Cr-catalyzed reaction is carried out in the presence of Jacobsen's Salen ligand, the regiochemical outcome of the reaction is again reversed, and syn-alk-1-en-3,4-diols are formed in high ee's.

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11

Omae, Iwao. "ChemInform Abstract: Carbonyl Group-Containing Organometallic Intramolecular-Coordination Five-Membered Ring Compounds." ChemInform 41, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.201031227.

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12

Holloway, Clive E., and Milan Melník. "Organometallic and carbonyl compounds of cadmium: analysis of crystallographic and structural data." Journal of Organometallic Chemistry 522, no. 2 (1996): 167–75. http://dx.doi.org/10.1016/0022-328x(96)06157-8.

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13

Motherwell, William B. "Curiosity and simplicity in the invention and discovery of new metal-mediated reactions for organic synthesis." Pure and Applied Chemistry 74, no. 1 (2002): 135–42. http://dx.doi.org/10.1351/pac200274010135.

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Two organometallic themes of current interest are presented. The scope and generality of the reductive deoxygenation of carbonyl compounds to organozinc carbenoids using zinc in combination with a silicon electrophile is discussed. Alkoxycyclopropanation can be achieved using orthoformates as substrates. Preliminary observations on the development of a rhodium-catalyzed tandem hydrosilylationintramolecular aldol sequence are discussed.

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14

Chan, T. H., C. J. Li, M. C. Lee, and Z. Y. Wei. "1993 R.U. Lemieux Award Lecture Organometallic-type reactions in aqueous media—a new challenge in organic synthesis." Canadian Journal of Chemistry 72, no. 5 (1994): 1181–92. http://dx.doi.org/10.1139/v94-151.

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The development of organometallic-type reactions in aqueous media is reviewed. Coupling reactions of allyl halides with carbonyl compounds mediated by zinc, or tin, or indium in aqueous media to give homoallylic alcohols are discussed. The stereochemical outcome is compared with similar reactions in organic solvents. A concise synthesis of (+)-muscarine is used to illustrate the usefulness of aqueous organometallic-type reactions in organic synthesis. The procedure to protect–deprotect hydroxy functional groups may not be necessary in these reactions. An application in the carbohydrate area is demonstrated with the synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). The mechanistic possibilities of organometallic-type reactions in aqueous media are outlined.

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15

Narayanaperumal, Senthil, Ricardo S. Schwab, Wystan K. O. Teixeira, and Danilo Yano de Albuquerque. "Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds." Synthesis 52, no. 13 (2020): 1855–73. http://dx.doi.org/10.1055/s-0039-1690847.

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Enantiomerically enriched diaryl, aryl heteroaryl, and diheteroaryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

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16

Ham, Won-Hun, Jae-Gwon Yang, Mi-Jeoung Lee, Jung-Nam Song, Ki-Su Kim, and Yun-Sung Chung. "Regioselective allenylation of carbonyl compounds with propargylic organometallics." Archives of Pharmacal Research 16, no. 3 (1993): 257–58. http://dx.doi.org/10.1007/bf02974493.

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17

VanAtta, Sky L., Brian A. Duclos, and David B. Green. "Microwave-Assisted Synthesis of Group 6 (Cr, Mo, W) Zerovalent Organometallic Carbonyl Compounds." Organometallics 19, no. 12 (2000): 2397–99. http://dx.doi.org/10.1021/om990977g.

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18

Noyori, Ryoji, and Masato Kitamura. "Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and Amplification." Angewandte Chemie International Edition in English 30, no. 1 (1991): 49–69. http://dx.doi.org/10.1002/anie.199100491.

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19

Holloway, Clive E., and Milan Melnik. "Manganese carbonyl and organometallic compounds: Analysis and classification of crystallographic and structural data." Journal of Organometallic Chemistry 396, no. 2-3 (1990): 129–246. http://dx.doi.org/10.1016/0022-328x(90)85465-b.

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20

Gao, Shang, Yang Liu, Yuandong Shao, Dayong Jiang, and Qian Duan. "Iron carbonyl compounds with aromatic dithiolate bridges as organometallic mimics of [FeFe] hydrogenases." Coordination Chemistry Reviews 402 (January 2020): 213081. http://dx.doi.org/10.1016/j.ccr.2019.213081.

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21

Dembinski, Roman, Renata Kaczmarek, Dariusz Korczyński, and Karolina Królewska-Golińska. "Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl Alkynyl Modified 2′-Deoxyuridines." Proceedings 22, no. 1 (2019): 62. http://dx.doi.org/10.3390/proceedings2019022062.

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In continuation of synthetic pursuit of metallo-nucleosides, in particular dicobalt hexacarbonyl 5-alkynyl-2′-deoxyuridines, novel compounds with alkynyl groups were synthesized, starting from 5-iodo-2′-deoxyuridine. Reactions of dicobalt octacarbonyl [Co2(CO)8] with 2′-deoxy-5-oxopropynyluridines and related compounds gave dicobalt hexacarbonyl nucleoside complexes (83–31%). The growth inhibition of HeLa and K562 cancer cell lines by organometallic nucleosides was examined and compared to that by alkynyl nucleoside precursors. Coordination of the dicobalt carbonyl moiety to the 2′-deoxy-5-alkynyluridines led to a significant increase in its cytotoxic potency. The cobalt compounds antiproliferative activities against the HeLa cell line and the K562 cell line will be described. Coordination of an acetyl-substituted cobalt nucleoside was expanded using the 1,1-bis(diphenylphosphino)methane (dppm) ligand, resulting in cytotoxicity at comparable levels. The formation of reactive oxygen species in the presence of cobalt compounds was determined in K562 cells. The results indicate that the mechanism of action for most antiproliferative cobalt compounds may be related to the induction of oxidative stress.

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22

Kimura, Tsutomu, Koto Sekiguchi, Akane Ando, and Aki Imafuji. "Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes." Beilstein Journal of Organic Chemistry 17 (May 28, 2021): 1352–59. http://dx.doi.org/10.3762/bjoc.17.94.

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A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch–Buttenberg–Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations.

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23

KAUFFMANN, T., J. JORDAN, and K. U. VOSS. "ChemInform Abstract: Transition-Metal-Activated Organic Compounds. Part 35. Methylating Reductive Dimerization of Aromatic Carbonyl Compounds, a Novel Organometallic Reaction." ChemInform 22, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199144097.

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24

Li, Lian-Hai, and Tak Hang Chan. "Organometallic reactions in aqueous media. Antimony-mediated allylation of carbonyl compounds with fluoride salts." Tetrahedron Letters 41, no. 26 (2000): 5009–12. http://dx.doi.org/10.1016/s0040-4039(00)00795-4.

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25

HOLLOWAY, C. E., and M. MELNIK. "ChemInform Abstract: Organometallic and Carbonyl Compounds of Cadmium: Analysis of Crystallographic and Structural Data." ChemInform 28, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199701318.

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26

Chan, Tak Hang, and Chao Jun Li. "Organometallic reactions in aqueous medium. Conversion of carbonyl compounds to 1,3-butadienes or vinyloxiranes." Organometallics 9, no. 10 (1990): 2649–50. http://dx.doi.org/10.1021/om00160a008.

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27

Lu, Wenshuo, Jihai Ma, Yang, and Tak Hang Chan. "Organometallic Reactions in Aqueous Media. Indium-Mediated 1,3-Butadien-2-ylation of Carbonyl Compounds." Organic Letters 2, no. 22 (2000): 3469–71. http://dx.doi.org/10.1021/ol000239k.

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28

Li, Lian-Hai, and Tak Hang Chan. "Organometallic reactions in aqueous media Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates." Canadian Journal of Chemistry 79, no. 11 (2001): 1536–40. http://dx.doi.org/10.1139/v01-128.

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Commercial antimony metal, in aqueous 1 M H(D)Cl solution, reacts with allyl bromide and aldehydes to give the corresponding homoallylic alcohols in good yield. The reaction proceeds through the formation of allylstibine intermediates. The structures of the allylstibine intermediates are likely to be allylstibine dibromide and diallylstibine bromide.Key words: allylation reaction, aqueous organometallic reactions, homoallylic alcohols, allylstibine dibromide, diallylstibine bromide.

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29

Siuzdak, Gary, Sebastian V. Wendeborn, and K. C. Nicolaou. "Cationization of organometallo carbonyl compounds by fast ion bombardment." International Journal of Mass Spectrometry and Ion Processes 112, no. 1 (1992): 79–91. http://dx.doi.org/10.1016/0168-1176(92)87033-b.

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30

Serdyuk, Olga, Igor Trushkov, Maxim Uchuskin, and Vladimir Abaev. "Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds." Synthesis 51, no. 04 (2019): 787–815. http://dx.doi.org/10.1055/s-0037-1611702.

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Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefination4 Reactions Involving the Enone Conjugate System С=С–С=О4.1 Reactions with 1,2-Dinucleophiles4.2 Reactions with Compounds Bearing an Active Methylene Group4.3 Reactions with 1,3-Dinucleophiles4.4 Reactions with 1,4-Dinucleophiles5 Functionalization of the Enone Methylene Group C(O)–CH2R5.1 Acylation/Crotonic Condensation and Related Transformations5.2 Enolization6 Functionalization of the Indole Core6.1 [4+2] Cycloaddition6.2 [3+3] Annulation6.3 Electrocyclic Reactions7 Miscellaneous8 Conclusions

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31

Gebhardt, Benjamin, Zois Syrgiannis, Claudia Backes, Ralf Graupner, Frank Hauke, and Andreas Hirsch. "Carbon Nanotube Sidewall Functionalization with Carbonyl Compounds—Modified Birch Conditions vs the Organometallic Reduction Approach." Journal of the American Chemical Society 133, no. 20 (2011): 7985–95. http://dx.doi.org/10.1021/ja2016872.

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32

HOLLOWAY, C. E., and M. MELNIK. "ChemInform Abstract: Manganese Carbonyl and Organometallic Compounds: Analysis and Classification of Crystallographic and Structural Data." ChemInform 22, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199102379.

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33

NOYORI, R., and M. KITAMURA. "ChemInform Abstract: Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication and Amplification." ChemInform 22, no. 14 (2010): no. http://dx.doi.org/10.1002/chin.199114331.

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34

Ugo, R., C. Dossi, and R. Psaro. "Molecular metal carbonyl clusters and volatile organometallic compounds for tailored mono and bimetallic heterogeneous catalysts." Journal of Molecular Catalysis A: Chemical 107, no. 1-3 (1996): 13–22. http://dx.doi.org/10.1016/1381-1169(95)00162-x.

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35

Jonas, Volker, Gernot Frenking, and Manfred T. Reetz. "Theoretical Studies of Organometallic Compounds. XVII. Mechanism of the Chelation Controlled Addition of CH3TiCl3 to .alpha.-Alkoxy Carbonyl Compounds. A Theoretical Study." Organometallics 14, no. 11 (1995): 5316–24. http://dx.doi.org/10.1021/om00011a057.

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36

Lu, Wenshuo, Jihai Ma, Yang Yang, and Tak Hang Chan. "ChemInform Abstract: Organometallic Reactions in Aqueous Media. Indium-Mediated 1,3-Butadien-2-ylation of Carbonyl Compounds." ChemInform 32, no. 12 (2001): no. http://dx.doi.org/10.1002/chin.200112067.

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37

Li, Lian-Hai, and Tak Hang Chan. "ChemInform Abstract: Organometallic Reactions in Aqueous Media. Antimony-Mediated Allylation of Carbonyl Compounds with Fluoride Salts." ChemInform 31, no. 40 (2000): no. http://dx.doi.org/10.1002/chin.200040054.

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38

Xu, Liancai, Qian-shu Li, Yaoming Xie, R. Bruce King, and Henry F. Schaefer. "Prospects for Making Organometallic Compounds with BF Ligands: Fluoroborylene Iron Carbonyls." Inorganic Chemistry 49, no. 3 (2010): 1046–55. http://dx.doi.org/10.1021/ic901964f.

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39

Urbán, Béla, Máté Papp, and Rita Skoda-Földes. "Carbonylation of Aryl Halides in the Presence of Heterogeneous Catalysts." Current Green Chemistry 6, no. 2 (2019): 78–95. http://dx.doi.org/10.2174/2213346106666190321141550.

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Palladium-catalyzed carbonylation in the presence of organic and organometallic nucleophiles serves as a powerful tool for the conversion of aryl/alkenyl halides or halide equivalents to carbonyl compounds and carboxylic acid derivatives. To circumvent the difficulties in product separation and recovery and reuse of the catalysts, associated with homogeneous reactions, supported counterparts of the homogeneous palladium catalysts were developed. The review intends to summarize the huge development that has been witnessed in recent years in the field of heterogeneous carbonylation. A great plethora of supports, organic modifiers on solid surfaces stabilizing metal particles, transition metal precursors, as well as alternative sources for CO was investigated. In most cases, careful optimization of reaction conditions was carried out. Besides simple model reactions, the synthesis of carbonyl compounds and carboxylic acid derivatives from substrates with different functionalities was performed. In some cases, causes of palladium leaching were clarified with detailed investigations. The advantages of immobilized catalysts were shown by several examples. The possibility of catalystrecycling was proved besides proving that metal contamination of the products could often be kept below the detection limit. At the same time, detailed investigations should be carried out to gain a better insight into the real nature of these processes.

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40

UGO, R., C. DOSSI, and R. PSARO. "ChemInform Abstract: Molecular Metal Carbonyl Clusters and Volatile Organometallic Compounds for Tailored Mono- and Bimetallic Heterogeneous Catalysts." ChemInform 27, no. 42 (2010): no. http://dx.doi.org/10.1002/chin.199642255.

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41

Li, Lian-Hai, and Tak Hang Chan. "Organometallic reactions in aqueous media Antimony-mediated allylation of carbonyl compounds and the nature of allylstibine intermediates." Canadian Journal of Chemistry 79, no. 11 (2001): 1536–40. http://dx.doi.org/10.1139/cjc-79-11-1536.

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42

Endrich, K., P. Alburquerque, R. P. Korswagen, and M. L. Ziegler. "Über die Reaktionen von Phosphoryliden mit homodinuklearen Organometallverbindungen des Molybdän und Wolfram / On the Reaction of Phosphorylides with Homodinuclear Organometallic Compounds of Molybdenum and Tungsten." Zeitschrift für Naturforschung B 43, no. 10 (1988): 1293–306. http://dx.doi.org/10.1515/znb-1988-1015.

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We report first the complete study of the reactions of [CpMo(CO)2]2 (Mo≡Mo) (1, Cp = η5-C5H5) with salt-free phosphorus ylides Ph3P=CHR (2, Ph = C6H5; R = H (2a), CH3 (2b), C3H7 (2c), C6H5 (2d)) and with the Nal-adducts of the ylides Ph3P=CMe2 (Me = CH3), PhMe2P=CH2 and (PhO)3P=CH2. With 2, products of the type Cp(CO)2LMo-MoL(CO)2Cp (7, L = ylide) were obtained, and the salt adducts gave addition compounds of the type Cp(CO)2LMo-MoL(CO)2Cp-2NaI (12, L = ylide). These very reactive products represent novel bisphosphonioalkyl complexes, and were characterized by IR, mass and 1H NMR spectrometry. The reaction of 1 with hexaphenylcarbodiphosphorane, C(PPh3)2, leads to a novel double addition product, Cp2Mo2(CO)4[C(PPh3)2]2 (14). Some reactions of compounds 7, 12 and 14 were also studied; 7d (L = CHPh -PPh3) reacts with NaNH2 yielding ammonia and the disodium salt of the novel dianionic complex [CpMo(CO)2(CPh-PPh3)]22- (15); 7a (L = CH2-PPh3) reacts with CH3I forming CpMo(CO)3CH3 and traces of CpMo(CO)2(PPh3)I; all compounds of types 7,12 and 14 react with adsorbents (Silica-gel, Al2O3, etc.); thus chromatography is impossible, even under strict protection from air and humidity. A study of the processes occurring during chromatography under various conditions and the resulting products are also reported and discussed. [CpW(CO)3]2 (18) reacts with 2a forming also a bisphosphonioalkyl complex [CpW(CO)2L]2(L = CH2=PPh3); in this case, the ylide substitutes two carbonyl groups in 18. The compounds [Cp*M(CO)2]2 (M≡M) (Cp* = C5Me5 ; M = Cr, W) apparently do not react with phosphorous ylides; the corresponding Mo compound, [Cp*Mo(CO)2]2 , does react, but only the new mono-nuclear complex Cp*Mo(CO)2(PPh3)Cl (22) could be isolated.

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43

Zambroń, Bartosz K. "Internal Chelation within Functionalized Organoindium Reagents: Prospects for Regio- and Stereocontrol in the Allylation, Propargylation and Allenylation of Carbonyl Compounds." Synthesis 52, no. 08 (2020): 1147–80. http://dx.doi.org/10.1055/s-0039-1690817.

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The low basicity, selective nucleophilicity, and mildness of organoindium compounds allow for the incorporation of many important yet sensitive functional groups into their structure, including examples capable of intramolecularly chelating the indium center within these reagents. The specific nature of such chelated organoindiums causes the reactions involving them to proceed in a unique manner, often with regio- and stereoselectivity inaccessible with simple organometallic reagents. This review covers the rare examples of regio- and stereoselective allylation, propargylation, and allenylation of carbonyl compounds with chelated organoindiums, including brief descriptions of the applications of the resulting adducts in the asymmetric synthesis of natural products and synthetic targets of biological and medicinal interest.1 Introduction2 Internal Chelation Control in the Allylation Processes2.1 Allylindiums with a Chelating Center at the γ-Position2.2 Allylindiums with a chelating Center at the δ-Position2.3 Allylindiums with a Chelating Center at ε- and ζ-Positions2.4 Allylindiums with a Chelating Center at γ′- and δ′-Positions3 Internal Chelation Control in Propargylation and Allenylation Processes3.1 Additions of Chelated Allenylindiums3.2 Additions of Chelated Propargylindiums4 Conclusion

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Cesari, Cristiana, Riccardo Conti, Andrea Cingolani, et al. "Synthesis and Reactivity of Poly(propyleneimine) Dendrimers Functionalized with Cyclopentadienone N-Heterocyclic-Carbene Ruthenium(0) Complexes." Catalysts 10, no. 2 (2020): 264. http://dx.doi.org/10.3390/catal10020264.

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Ligand design in metal chemistry is a fundamental step when pursuing compounds with specific reactivity. In this paper, the functionalization of the OH group in the lateral chain of the N-heterocyclic-carbene (NHC) ligand bound to a bis-carbonyl cyclopentadienone NHC ruthenium(0) complex allowed the decoration of five generations of poly(propyleneimine) (PPIs) dendrimers with up to 64 organometallic moieties. The coupling was achieved by employing carbonyldiimidazole and the formation of carbamate linkages between dendritic peripheral NH2 and lateral OH groups on ruthenium complexes. The synthetic procedure, chemical purification, and spectroscopic characterization of the five generations of dendrimers (3g1–5) are here described. The ruthenium-modified dendrimers were activated as catalysts in the transfer hydrogenation of the model compound 4-fluoroacetophenone in the presence of cerium ammonium nitrate as their mononuclear congeners. The catalytic activity, being similar for the five generations, shows a decrease if compared to mononuclear complexes. This detrimental effect might be ascribed to the –CH2NH– functionalization, largely present in dendrimer skeleton and that can compete with the hydrogen transfer mechanism, but also partially to a dendritic effect caused by steric encumbrance.

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45

Jurgens, Sophie, Fritz E. Kuhn, and Angela Casini. "Cyclometalated Complexes of Platinum and Gold with Biological Properties: State-of-the-Art and Future Perspectives." Current Medicinal Chemistry 25, no. 4 (2018): 437–61. http://dx.doi.org/10.2174/0929867324666170529125229.

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Background: The inherent problems accompanying chemotherapy necessitate the development of new anticancer approaches. The development of compounds that can disrupt cancerous cellular machinery by novel mechanisms, via interactions with proteins and non-canonical DNA structures (e.g. G-quadruplexes), as well as by alteration of the intracellular redox balance, is nowadays focus of intense research. In this context, organometallic compounds of the noble metals Pt and Au have become prominent experimental therapeutic agents. This review provides an overview of the Pt(II) and Au(III) cyclometalated compounds with a chelating ring containing a strong C-M σ -bond to improve the stability of the compounds with respect to ligand exchange reactions and biological reduction. Furthermore, these properties can be easily tuned by modification of either the anionic cyclometalated or the ancillary ligands. Special focus has been set to C^N, C^N^C, C^N^N and C^N^S platinum(II) and gold(III) pincer complexes regarding their synthesis and biological mechanisms of action as anticancer agents. Methods: A structured search of both chemical and medicinal databases for peerreviewed research literature has been conducted. The quality of retrieved papers was appraised using standard tools. The synthesis as well as the chemical and biological properties of the described compounds were carefully reviewed and described. The findings were outlined using a conceptual framework. Results: In this review we included 155 papers, the majority originating from high-impact papers on the synthesis and biological modes of platinum(II) and gold(III) compounds. Among them, 17 papers were highlighted to give an introduction to the use of Pt and Au compounds with medicinal properties, mainly focussing on coordination compounds. The synthesis and medicinal properties of organometallic compounds of various metals (such as Fe, Ru, Ti) were outlined in 51 papers. These compounds included metallocenes, metallo- arenes, metallo-carbonyls, metallo-carbenes (e.g. N-heterocyclic carbenes), and alkynyl complexes. The C^N, C^N^C, C^N^N and C^N^S pincer complexes of platinum( II) (46 papers) and gold(III) (44 papers) were discussed concerning their synthesis, stability and advantages to develop therapeutic compounds. We strove to show the consistent development of C^N, C^N^C, C^N^N and C^N^S platinum(II) and gold(III) pincer complexes regarding their synthesis and biological modes from the early beginnings to the most recent findings. Conclusion: This review supplies a profound overview of the development of organometallic compounds for medicinal purposes, setting special focus to the synthesis and stability of C^N, C^N^C, C^N^N and C^N^S pincer complexes of platinum(II) and gold(III) and their use as anticancer agents.

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de las Heras, María A., Juan J. Vaquero, JoséL García Navio, and Julio Alvarez-Builla. "Synthesis of carbonyl and dicarbonyl compounds from organometallic reagents and N-imidazolium-N-methyl amides and bis-amides." Tetrahedron 52, no. 45 (1996): 14297–310. http://dx.doi.org/10.1016/0040-4020(96)00882-4.

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47

Santori, Gerardo F., Mónica L. Casella, and Osmar A. Ferretti. "Hydrogenation of carbonyl compounds using tin-modified platinum-based catalysts prepared via surface organometallic chemistry on metals (SOMC/M)." Journal of Molecular Catalysis A: Chemical 186, no. 1-2 (2002): 223–39. http://dx.doi.org/10.1016/s1381-1169(02)00188-7.

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48

Chan, Tak Hang, Yang, and Chao Jun Li. "Organometallic Reactions in Aqueous Media. The Nature of the Organotin Intermediate in the Tin-Mediated Allylation of Carbonyl Compounds." Journal of Organic Chemistry 64, no. 12 (1999): 4452–55. http://dx.doi.org/10.1021/jo9901337.

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49

Li, Lian-Hai, and Tak Hang Chan. "ChemInform Abstract: Organometallic Reactions in Aqueous Media - Antimony-Mediated Allylation of Carbonyl Compounds and the Nature of Allylstibine Intermediates." ChemInform 33, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.200226068.

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50

Lucas, C. Robert. "Thioether complexes of tungsten hexacarbonyl." Canadian Journal of Chemistry 64, no. 9 (1986): 1758–63. http://dx.doi.org/10.1139/v86-290.

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The preparation of a series of organic and organometallic thioethers R3MSR′ (M = C, Si, Ge, or Sn) is reported. From these, several new compounds of type 1 are synthesized, some of which contain para-substituted aryl functions for R′ and R. In hexane solution in the carbonyl stretching region of the ir and in the uv there is evidence for a degree of multiple bonding, at least in the M—S—W—CO portion of these molecules. Multiple bonding extending into aromatic R or R′ is small or non-existent and cannot be assessed precisely because of spontaneous decomposition of the complexes. All the complexes undergo a thermally initiated decomposition, the ease of which depends on the nature of R, R′, and M. The unusual W(I) thiolate cis-[(CO)4W-μ-SR′]2 is the thermal decomposition product.

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