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Journal articles on the topic 'Oxidation Transition metal halides'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Yadav, Sangeeta, Sudesh T. Manjare, Harkesh B. Singh, and Ray J. Butcher. "Transition metal mediated formation of dicationic diselenides stabilised by N-heterocyclic carbenes: designed synthesis." Dalton Transactions 45, no. 30 (2016): 12015–27. http://dx.doi.org/10.1039/c6dt01425a.

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2

Rossi, Laura, and A´ngela Sua´rez. "Transition metal halides as catalysts in the oxidation reaction of sulfides into sulfoxides." Sulfur Letters 25, no. 3 (January 2002): 123–27. http://dx.doi.org/10.1080/02786110212863.

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3

Swarnakar, Anindya K., Michael J. Ferguson, Robert McDonald, and Eric Rivard. "Transition metal-mediated donor–acceptor coordination of low-oxidation state Group 14 element halides." Dalton Transactions 45, no. 14 (2016): 6071–78. http://dx.doi.org/10.1039/c5dt03018h.

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4

Wang, Ying, Yang Wang, Kai Jiang, Qian Zhang, and Dong Li. "Transition-metal-free oxidative C5 C–H-halogenation of 8-aminoquinoline amides using sodium halides." Organic & Biomolecular Chemistry 14, no. 43 (2016): 10180–84. http://dx.doi.org/10.1039/c6ob02079h.

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5

Bortoluzzi, Marco, Eleonora Ferretti, Fabio Marchetti, Guido Pampaloni, and Stefano Zacchini. "A structurally-characterized NbCl5–NHC adduct." Chem. Commun. 50, no. 34 (2014): 4472–74. http://dx.doi.org/10.1039/c4cc01575d.

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6

Sellmann, Dieter, Gerhard Freyberger, and Matthias Moll. "Übergangsmetallkomplexe mit Schwefelliganden, XLVIa. Zn-, Cd-, Hg-, Sn-, Pb-, Sb-, Bi- und Ti-Komplexe mit den zwei- und vierzähnigen Thiolatliganden 'buS2'2- = 3,5-Di(t-butyl)benzol-1,2-dithiolat(2—), 'S4'2- = 1,2-Bis(2-mercaptophenylthio)ethan(2—) und 'buS4'2- = 1,2-Bis(3,5-di(t-butyl)-2-mercaptophenylthio)ethan(2–) / Transition Metal Complexes with Sulfur Ligands, XLVIa. Zn, Cd, Hg, Sn, Pb, Bi and Ti Complexes with the Bi- and Tetradentate Thiolato Ligands 'buS2'2- = 3,5-Di(t-butyl)benzene-1,2-dithiolate(2–), 'S4'2 = 1,2-Bis(2-mercaptophenylthio)ethane(2–) and 'buS4'2- = 1,2-Bis(3,5-di(t-butyl)-2-mercaptophenylthio)ethane(2 – )." Zeitschrift für Naturforschung B 44, no. 9 (September 1, 1989): 1015–22. http://dx.doi.org/10.1515/znb-1989-0905.

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Syntheses of neutral 'buS2'-, 'S4'- and 'buS4'- and of anionic .buS2-complexes with various main group and transition metals are described. The complexes were prepared by reacting the neutral sulfur ligands or their alkali salts with the metal halide or alkoxide. The ligands coordinate to metal ions in normal as well as high oxidation states. No redox reactions occur in the latter case. The complexes are usually soluble in organic solvents and were characterized by elemental analysis and spectroscopic means.

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7

Anuma, Saroja, and Badekai Ramachandra Bhat. "Nanographene Sheet Immobilized Transition Metal Complexes for C-C Coupling Reactions." International Journal of Engineering & Technology 7, no. 4.5 (September 22, 2018): 431. http://dx.doi.org/10.14419/ijet.v7i4.5.20199.

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Transition metal Schiff base complexes covalently immobilized on the surface of amino functionalized graphene sheet to catalyze C-C coupling reaction is reported. Graphene sheet which synthesized using mechanical exfoliation and then by differential oxidative reduction phenomenon of graphite. The schiff base ligand is prepared using aldehyde and amino groups containing compounds which further treated with metal salts to form metal complexes. The as-synthesized metal complexes was then incorporated into amino functionalized nanosheets which are characterized using different spectrochemical techniques. The catalytic investigation of the as-prepared catalyst were done by the cross coupling of aryl halides and aryl boronic acids to form biaryls as product in C-C cross coupling reaction. The yield of the products were high and selective which were analyzed using Gas chromatography technique. The advantage of this catalyst is high stability, recyclability easy recovery of catalyst, environmentally benign and mild reaction condition.

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8

Malisch, Wolfgang, Katharina Thirase, and Joachim Reising. "Ubergangsmetall-substituierte Phosphane, Arsane und Stibane, LX [1]. Ferrio-(thiocarbamoyl)phosphane Cp(OC)2 Fe-P(Mes)[C(=S)-N(R)H] (R = Me, Et, f-Bu): Aufbau aus dem Ferrio-mesitylphosphan Cp(OC)2 Fe-P(Mes)H und Organoisothiocyanaten sowie Quaternisierung mit Alkylhalogeniden und Oxidation mit Schwefel / Transition Metal Substituted Phosphanes, Arsanes and Stibanes, LX [1]. Ferrio-(thiocarbamoyl)phosphanes Cp(OC)2Fe-P(Mes)[C(=S)-N(R)H] (R= Me, Et, r-Bu): Build-up from the Ferrio-mesitylphosphane Cp(OC)2Fe-P(Mes)H and Organoisothiocyanates, Quatemization with Alkyl Halides and Oxidation with Sulfur." Zeitschrift für Naturforschung B 53, no. 10 (October 1, 1998): 1084–91. http://dx.doi.org/10.1515/znb-1998-1002.

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AbstractArsane und Stibane, LX [1]. Ferrio-(thiocarbamoyl)phosphane Cp(OC)2Fe-P(Mes)[C(=S)-N(R)H] (R = Me, Et, f-Bu): Aufbau aus dem Ferrio-mesitylphosphan Cp(OC)2Fe-P(Mes)H und Organoisothiocyanaten sowie Quaternisierung mit Alkylhalogeniden und Oxidation mit Schwefel Transition Metal Substituted Phosphanes, Arsanes and Stibanes, LX [1]. Ferrio-(thiocarbamoyl)phosphanes Cp(OC)2Fe-P(Mes)[C(=S)-N(R)H] (R= Me, Et, r-Bu): Build-up from the Ferrio-mesitylphosphane Cp(OC)2Fe-P(Mes)H and Organoisothiocyanates, Quatemization with Alkyl Halides and Oxidation with Sulfur The ferrio-phosphane Cp(OC)2Fe-P(Mes)H (4), obtained by deprotonation of the me-sitylphosphane iron complex {Cp(OC)2 [H2(Mes)P]Fe}BF4 (3), reacts with the organoiso thiocyanates RNCS (R = Me, Et, Ph) (5a -c) to give the functionalized ferrio-phosphanes Cp(OC)2Fe-P(Mes)[C(=S)-N(R)H] (6a-c). Quatemization of 6a,b at the phosphorus atom with the alkyl halides R′-Hal (R1 = Me, Et, CH2 Ph) (7a-c) yields the complexes {Cp(OC)2Fe-P(Mes)(R′)[C(=S)-N(H)(R)]}Hal (8a-d), whereas oxidation with elemental sulfur affords the ferrio-thiophosphoranes Cp(OC)2Fe-P(=S)(Mes)[C(=S)-N(R)H] (R = Me, Et) (10a,b). 10b is alkylated with Mel to give {Cp(OC)2Fe-P(SMe)(Mes)[C(=S)-N(Et)H]}I (11). The structure of 8b has been determined by X-ray analysis.

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9

Welin, Eric R., Chip Le, Daniela M. Arias-Rotondo, James K. McCusker, and David W. C. MacMillan. "Photosensitized, energy transfer-mediated organometallic catalysis through electronically excited nickel(II)." Science 355, no. 6323 (January 26, 2017): 380–85. http://dx.doi.org/10.1126/science.aal2490.

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Transition metal catalysis has traditionally relied on organometallic complexes that can cycle through a series of ground-state oxidation levels to achieve a series of discrete yet fundamental fragment-coupling steps. The viability of excited-state organometallic catalysis via direct photoexcitation has been demonstrated. Although the utility of triplet sensitization by energy transfer has long been known as a powerful activation mode in organic photochemistry, it is surprising to recognize that photosensitization mechanisms to access excited-state organometallic catalysts have lagged far behind. Here, we demonstrate excited-state organometallic catalysis via such an activation pathway: Energy transfer from an iridium sensitizer produces an excited-state nickel complex that couples aryl halides with carboxylic acids. Detailed mechanistic studies confirm the role of photosensitization via energy transfer.

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10

Beck, Johannes, and Joerg Wetterau. "Chalcogen Polycations by Oxidation of Elemental Chalcogens with Transition Metal Halides: Synthesis and Crystal Structure of [Se17][WCl6]2." Inorganic Chemistry 34, no. 24 (November 1995): 6202–4. http://dx.doi.org/10.1021/ic00128a036.

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11

Gooßen, Lukas J., Käthe Gooßen, Nuria Rodríguez, Mathieu Blanchot, Christophe Linder, and Bettina Zimmermann. "New catalytic transformations of carboxylic acids." Pure and Applied Chemistry 80, no. 8 (January 1, 2008): 1725–33. http://dx.doi.org/10.1351/pac200880081725.

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A series of metal-catalyzed processes are presented, in which carboxylic acids act as sources of either carbon nucleophiles or electrophiles, depending on the catalyst employed, the mode of activation, and the reaction conditions. A first reaction mode is the addition of carboxylic acids or amides over C-C multiple bonds, giving rise to enol esters or enamides, respectively. The challenge here is to control both the regio- and stereoselectivity of these reactions by the choice of the catalyst system. Alternatively, carboxylic acids can efficiently be decarboxylated using new Cu catalysts to give aryl-metal intermediates. Under protic conditions, these carbon nucleophiles give the corresponding arenes. If carboxylate salts are employed instead of the free acids, the aryl-metal species resulting from the catalytic decarboxylation can be utilized for the synthesis of biaryls in a novel cross-coupling reaction with aryl halides, thus replacing stoichiometric organometallic reagents. An activation with coupling reagents or simple conversion to esters allows the oxidative addition of carboxylic acids to transition-metal catalysts under formation of acyl-metal species, which can either be reduced to aldehydes, or coupled with nucleophiles. At elevated temperatures, such acyl-metal species decarbonylate, so that carboxylic acids become synthetic equivalents for aryl or alkyl halides, e.g., in Heck reactions.

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12

Chen, Mingwei, Jinyu Hu, Xiaoli Tang, and Qiming Zhu. "Piperazine as an Inexpensive and Efficient Ligand for Pd-Catalyzed Homocoupling Reactions to Synthesize Bipyridines and Their Analogues." Current Organic Synthesis 16, no. 1 (February 4, 2019): 173–80. http://dx.doi.org/10.2174/1570179415666180913131905.

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Aim and Objective: The synthesis of bipyridines, especially 2, 2’-bipyridines, remains challenging because the catalytic cycle can be inhibited due to coordination of bipyridine to transition metal. Thus, the development of efficient methods for the synthesis of bipyridines is highly desirable. In the present work, we presented a promising approach for preparation of bipyridines via a Pd-catalyzed reductive homocoupling reaction with simple piperazine as a ligand. Materials and Methods: Simple and inexpensive piperazine was used as a ligand for Pd-catalyzed homocoupling reaction. The combination of Pd(OAc)2 and piperazine in dimethylformamide (DMF) was observed to form an excellent catalyst and efficiently catalyzed the homocoupling of azaarenyl halides, in which DMF was used as the solvent without excess reductants although stoichiometric reductant was generally required to generate the low-oxidation-state active metal species in the catalytic cycles. </P><P> Results: In this case, good to excellent yields of bipyridines and their (hetero) aromatic analogues were obtained in the presence of 2.5 mol% of Pd(OAc)2 and 5 mol% of piperazine, using K3PO4 as a base in DMF at 140°C. Conclusion: According to the results, piperazine as an inexpensive and efficient ligand was used in the Pd(OAc)2-catalyzed homocoupling reaction of heteroaryl and aryl halides. The coupling reaction was operationally simple and displayed good substrate compatibility.

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13

Shaughnessy, Kevin H. "Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions." Current Organic Chemistry 24, no. 3 (May 4, 2020): 231–64. http://dx.doi.org/10.2174/1385272824666200211114540.

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Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

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14

Peng, Zhihua, Na Li, Xinyang Sun, Fang Wang, Lanjian Xu, Cuiyu Jiang, Linhua Song, and Zi-Feng Yan. "The transition-metal-catalyst-free oxidative homocoupling of organomanganese reagents prepared by the insertion of magnesium into organic halides in the presence of MnCl2·2LiCl." Org. Biomol. Chem. 12, no. 39 (2014): 7800–7809. http://dx.doi.org/10.1039/c4ob01235f.

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15

BECK, J., and J. WETTERAU. "ChemInform Abstract: Chalcogen Polycations by Oxidation of Elemental Chalcogens with Transition Metal Halides: Synthesis and Crystal Structure of (Se17) ( WCl6)2." ChemInform 27, no. 9 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199609026.

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16

Torres, Gerardo M., Yi Liu, and Bruce A. Arndtsen. "A dual light-driven palladium catalyst: Breaking the barriers in carbonylation reactions." Science 368, no. 6488 (April 16, 2020): 318–23. http://dx.doi.org/10.1126/science.aba5901.

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Transition metal–catalyzed coupling reactions have become one of the most important tools in modern synthesis. However, an inherent limitation to these reactions is the need to balance operations, because the factors that favor bond cleavage via oxidative addition ultimately inhibit bond formation via reductive elimination. Here, we describe an alternative strategy that exploits simple visible-light excitation of palladium to drive both oxidative addition and reductive elimination with low barriers. Palladium-catalyzed carbonylations can thereby proceed under ambient conditions, with challenging aryl or alkyl halides and difficult nucleophiles, and generate valuable carbonyl derivatives such as acid chlorides, esters, amides, or ketones in a now-versatile fashion. Mechanistic studies suggest that concurrent excitation of palladium(0) and palladium(II) intermediates is responsible for this activity.

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17

Schäffer, Claus E., Christian Anthon, and Jesper Bendix. "Bridging Kohn - Sham DFT and the Angular Overlap Model. Ligand-Field Parameters and Bond Covalencies in Tetrahedral Complexes." Australian Journal of Chemistry 62, no. 10 (2009): 1271. http://dx.doi.org/10.1071/ch09335.

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Kohn–Sham density functional theory (DFT), constrained by the average-of-configuration computations, allows the valence shell of regular tetrahedral chlorido complexes of a complete series of 3d transition metal ions to be orbitally compared. The concept of classificational parentage provides a handle on the discussion of the energetic ordering of all the valence orbitals and illuminates an almost identical ordering for all the systems. Only the participation of the metal 4s orbital in bonding causes a few minor fluctuations. The partially filled ‘3d’ molecular orbitals sit in an energy window framed by completely filled ‘ligand orbitals’ on the low-energy side and an empty metal ‘4s’ orbital on the high-energy side. Regular tetrahedral symmetry requires the halides to be linearly ligating and this property is stable within the ‘experimental’ uncertainty for small distortions. By lowering the symmetry towards the planar configuration, keeping the equivalence of the ligands stable, the information content of the computations was doubled and the angular overlap energy parameters referring to the individual ligands obtained. The orbital energies of the partially filled shell depend linearly on the Angular Overlap Model (AOM) parameters eλ, the slope being the sum of the squares of the single-ligand λ angular overlaps (λ = σ and π). Mulliken population analysis shows the contents of the appropriate ligand orbitals in the ‘d’ orbitals to vary in parallel with the molecular orbital AOM energies and to increase pronouncedly with the oxidation number z. Results for tetraoxidoferrate(vi) show a remarkable resemblance with the chloride complexes of even the divalent metal ions. However, although the bonding orbitals are more π-bonding, the totally symmetrical bonding orbitals use M_4s less in the oxido complex. The sensitivity of covalency and spectroscopic energy parameters towards radial distortions are examined and show Werner-type complexes and the high-valent FeO42– to behave somewhat differently.

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18

Keglevich, György, Réka Henyecz, and Zoltán Mucsi. "Focusing on the Catalysts of the Pd- and Ni-Catalyzed Hirao Reactions." Molecules 25, no. 17 (August 26, 2020): 3897. http://dx.doi.org/10.3390/molecules25173897.

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The Hirao reaction involving the phosphinoylation or phosphonation of aryl halides by >P(O)H reagents is a P–C bond forming transformation belonging to the recently very hot topic of cross-couplings. The Pd- or Ni-catalyzed variations take place via the usual cycle including oxidative addition, ligand exchange, and reductive elimination. However, according to the literature, the nature of the transition metal catalysts is not unambiguous. In this feature article, the catalysts described for the Pd(OAc)2-promoted cases are summarized, and it is concluded that the “(HOY2P)2Pd(0)” species (Y = aryl, alkoxy) is the real catalyst. In our model, the excess of the >P(O)H reagent served as the P-ligand. During the less studied Ni(II)-catalyzed instances the “(HOY2P)(−OY2P)Ni(II)Cl−” form was found to enter the catalytic cycle. The newest conclusions involving the exact structure of the catalysts, and the mechanism for their formation explored by us were supported by our earlier experimental data and theoretical calculations.

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19

Macgregor, Stuart A., and Klaus H. Moock. "Stabilization of High Oxidation States in Transition Metals. 2.1WCl6Oxidizes [WF6]-, but Would PtCl6Oxidize [PtF6]-? An Electrochemical and Computational Study of 5d Transition Metal Halides: [MF6]zversus [MCl6]z(M = Ta to Pt;z= 0, 1−, 2−)." Inorganic Chemistry 37, no. 13 (June 1998): 3284–92. http://dx.doi.org/10.1021/ic9605736.

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20

Nasir, H. M., T. A. Saki, and M. Y. Al-Luaibi. "Synthesis, identification and thermal study of some new inorganic polymers based on bis-dithiocarbamate ligands with silicone, tellurium and some transition metals." Innovaciencia Facultad de Ciencias Exactas Físicas y Naturales 7, no. 1 (October 25, 2019): 1–13. http://dx.doi.org/10.15649/2346075x.507.

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Introduction: In recent years, there has been considerable interest in dithiocarbamate complexes because of its diverse biological roles, very few reports have been made on polymeric bis- dithiocarbamate compounds with carbon chain of n-propyl or hexamethelene with transition metals in addition of the absence of any report of organosilicone or tellurium halides with such compounds Our interest in this report based on the preparation of new series of polymers with an expected activity as a fungi side compounds followed by the using of prepared amino compound as a hardners for epoxy paints Materials and Methods: A new polymers of the general structures –(MS2CNH(CH2)6NHCS2M-)n where [M= Cu, Cd, Mn and Zn] and –(M(R)2S2CNH(CH2)nNHCS2MR2-)m where [M= Si,R=CH 3 , n= 2 ,3 and 6 ; M=Te , R= Br , n= 2 ,3 and 6 ; M=Co, Ni R=Cl ; n= 6] have been prepared by reaction of MX2 where M= Ni ,Co, Cd , Mnor Zn , X= Cl ; M=Cu , X= SO4 , and dimethyl dichloro silane, tellurium tetrabromide with the corresponding sodium salts of bis-dithiocarbamateligands. Results and Discussion: Dimethyldichloro silane is a very sensitive material to O-H group, in addition to that, TeBr4 decomposed rapidlyin water so, a series solvents may be useful with such sensitive chemicals to water , in the other hand, dithiocarbamate ligands which is usually prepared in aqueous and alcoholic solution , must be prepared and isolated carefully to apply the other steps of synthesis using a chloroform solution as a solvent. It seems for the first view for dithiocarbamato ligands it may act as a bi dentate ligands using two sulphur donating atoms that is clearly appeared in common complexes such as diethyl dithiocarbamato or pipyridyl, morpholino dithiocarbamato with representation metal elements, even in such type of elements a sulfur bridges may formed. In this study, it showed clearly that Zinc and Cadimium polymers are diamagnetic polymers that is mean that these polymers are with oxidation state equal to (II) and a tetrahedral configuration Conclusions: The study showed that the new silicone polymers act as a stable polymers compared with others. All new polymers are of a high stability with large values of char contain with commercial epoxy. Among silicone polymers, the polymerwith carbon chain equal to 3 is more stable than that with 2 carbon atoms while the silicone polymer with 6 carbon atoms is the less stable one, may thermal treatment caused decomposition combined.

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21

Peng, Zhihua, Na Li, Xinyang Sun, Fang Wang, Lanjian Xu, Cuiyu Jiang, Linhua Song, and Zi-Feng Yan. "ChemInform Abstract: The Transition-Metal-Catalyst-Free Oxidative Homocoupling of Organomanganese Reagents Prepared by the Insertion of Magnesium into Organic Halides in the Presence of MnCl2·2LiCl." ChemInform 46, no. 11 (February 24, 2015): no. http://dx.doi.org/10.1002/chin.201511108.

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22

Fedorov, V. E., A. V. Mishchenko, and Vladimir P. Fedin. "Cluster Transition Metal Chalcogenide Halides." Russian Chemical Reviews 54, no. 4 (April 30, 1985): 408–23. http://dx.doi.org/10.1070/rc1985v054n04abeh003064.

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23

Böck, Barbara, Heinrich Nöth, and Ulrich Wietelmann. "Reactions of Amino-imino-boranes with Transition Metal Halides and Substituted Transition Metal Halides." Zeitschrift für Naturforschung B 56, no. 7 (July 1, 2001): 659–70. http://dx.doi.org/10.1515/znb-2001-0714.

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The aminoiminoborane tmp-B=NCMe3 (1) adds to TiBr4 or ZrCl4 in a 1:1 ratio while PdCl2 adds 1 in a 1:2 ratio. In these new compounds the NBN unit is almost linear and the configuration corresponds to an allene. On the other hand 1 and Ti(OR)4 compounds and Ti(NMe2)4 give N metallated diaminoboranes tmp-B(X)-NCMe3EX3 (X = OR, NMe2). Mixed compounds Ti(OR)3-nXn lead to diaminoboranes with BOR groups while the TiCl bond inserts into the B = N bond of 1 to produce tmp-BNMe2-NCMe3TiCl3. Hydrolysis of this compound leads to a spirocyclic dititanoxane with a short linear Ti-O-Ti bond and pentacoordinated Ti centers carrying two Cl atoms each. Spirocycles with a BN2E (E = Ti, Nb, Ta, Pd) unit are formed when 1 is allowed to react with TiCl4, NbCl5, TaCl5 and PdCl2. The palladium compound 16 is dimeric, and dimerization occurs via Pd-Cl bridges. The aminoiminoborane tmp-B=NC6H3-2,6-iPr2 reacts with the titanium compounds in the same manner as 1, however without formation of spirocycles.

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24

Petko, Dina, Samuel Koh, and William Tam. "Transition Metal-Catalyzed Reactions of Alkynyl Halides." Current Organic Synthesis 16, no. 4 (July 4, 2019): 546–82. http://dx.doi.org/10.2174/1570179416666190329200616.

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Background: Transition metal-catalyzed reactions of alkynyl halides are a versatile means of synthesizing a wide array of products. Their use is of particular interest in cycloaddition reactions and in constructing new carbon-carbon and carbon-heteroatom bonds. Transition metal-catalyzed reactions of alkynyl halides have successfully been used in [4+2], [2+2], [2+2+2] and [3+2] cycloaddition reactions. Many carbon-carbon coupling reactions take advantage of metal-catalyzed reactions of alkynyl halides, including Cadiot-Chodkiewicz, Suzuki-Miyaura, Stille, Kumada-Corriu and Inverse Sonogashira reactions. All the methods of constructing carbon-nitrogen, carbon-oxygen, carbon-phosphorus, carbon-sulfur, carbon-silicon, carbon-selenium and carbon-tellurium bonds employed alkynyl halides. Objective: The purpose of this review is to highlight and summarize research conducted in transition metalcatalyzed reactions of alkynyl halides in recent years. The focus will be placed on cycloaddition and coupling reactions, and their scope and applicability to the synthesis of biologically important and industrially relevant compounds will be discussed. Conclusion: It can be seen from the review that the work done on this topic has employed the use of many different transition metal catalysts to perform various cycloadditions, cyclizations, and couplings using alkynyl halides. The reactions involving alkynyl halides were efficient in generating both carbon-carbon and carbonheteroatom bonds. Proposed mechanisms were included to support the understanding of such reactions. Many of these reactions face retention of the halide moiety, allowing additional functionalization of the products, with some new products being inaccessible using their standard alkyne counterparts.

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25

Zhang, Hua, Renyi Shi, Anxing Ding, Lijun Lu, Borui Chen, and Aiwen Lei. "Transition-Metal-Free Alkoxycarbonylation of Aryl Halides." Angewandte Chemie International Edition 51, no. 50 (November 5, 2012): 12542–45. http://dx.doi.org/10.1002/anie.201206518.

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26

Lundgren, Rylan J., and Mark Stradiotto. "Transition-Metal-Catalyzed Trifluoromethylation of Aryl Halides." Angewandte Chemie International Edition 49, no. 49 (September 28, 2010): 9322–24. http://dx.doi.org/10.1002/anie.201004051.

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27

Zhang, Hua, Renyi Shi, Anxing Ding, Lijun Lu, Borui Chen, and Aiwen Lei. "Transition-Metal-Free Alkoxycarbonylation of Aryl Halides." Angewandte Chemie 124, no. 50 (November 5, 2012): 12710–13. http://dx.doi.org/10.1002/ange.201206518.

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28

Mészáros Szécs, K., T. Wadsten, A. Kovács, and G. Liptay. "Pyridine-type complexes of transition-metal halides." Journal of Thermal Analysis and Calorimetry 75, no. 3 (2004): 965–74. http://dx.doi.org/10.1023/b:jtan.0000027190.32572.8b.

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29

Thomas, J., G. Jezequel, and I. Pollini. "Optical properties of layered transition-metal halides." Journal of Physics: Condensed Matter 2, no. 24 (June 18, 1990): 5439–53. http://dx.doi.org/10.1088/0953-8984/2/24/015.

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30

Patil, S. F., and Munmum Nath. "Mutual-diffusion of some transition metal halides." Journal of Radioanalytical and Nuclear Chemistry Articles 198, no. 2 (December 1995): 423–28. http://dx.doi.org/10.1007/bf02036558.

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Liptay, G., G. Kenessey, and P. Bukovec. "Pyridine-type complexes of transition metal halides." Journal of Thermal Analysis 40, no. 2 (August 1993): 543–52. http://dx.doi.org/10.1007/bf02546624.

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Shi, Xiaolin, and Dayong Shi. "Recent Advances in Transition-Metal-Catalyzed Halides Formation." Current Organic Chemistry 22, no. 23 (December 17, 2018): 2229–55. http://dx.doi.org/10.2174/1385272822666181005111808.

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Kenessey, G., B. R. Carson, J. R. Allan, T. Wadsten, and G. Liptay. "Primary aliphatic amine complexes of transition-metal halides." Journal of thermal analysis 50, no. 1-2 (September 1997): 167–73. http://dx.doi.org/10.1007/bf01979559.

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34

Szécsényi, K. Mészáros, T. Wadsten, B. Carson, É. Bencze, G. Kenessey, and G. Liptay. "Pyridine-type complexes of transition-metal halides XIII." Thermochimica Acta 340-341 (December 1999): 255–61. http://dx.doi.org/10.1016/s0040-6031(99)00270-1.

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Van Vechten, D., N. Bauer, R. Cusick, and T. M. Dunn. "Chemiluminescence of transition-metal halides in active nitrogen." Journal of Physical Chemistry 89, no. 9 (April 1985): 1559–61. http://dx.doi.org/10.1021/j100255a001.

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Burdett, Jeremy K., and Gordon J. Miller. "Interstitial hydrogen in the early transition-metal halides." Journal of the American Chemical Society 109, no. 13 (June 1987): 4092–104. http://dx.doi.org/10.1021/ja00247a040.

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Shirakawa, Eiji, and Tamio Hayashi. "Transition-metal-free Coupling Reactions of Aryl Halides." Chemistry Letters 41, no. 2 (February 5, 2012): 130–34. http://dx.doi.org/10.1246/cl.2012.130.

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Karpov, V. V., V. A. Volkovich, I. B. Polovov, and O. I. Rebrin. "Solubility of Transition Metal Halides in Chloroaluminate Melts." ECS Transactions 64, no. 4 (August 15, 2014): 211–16. http://dx.doi.org/10.1149/06404.0211ecst.

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Coombs, Natalie D., Andreas Stasch, and Simon Aldridge. "Reactions of ‘GaI’ with organometallic transition metal halides." Inorganica Chimica Acta 361, no. 2 (January 2008): 449–56. http://dx.doi.org/10.1016/j.ica.2007.02.037.

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40

Torubaev, Yury, Alexander Pasynskii, and Pradeep Mathur. "Organotellurium halides: New ligands for transition metal complexes." Coordination Chemistry Reviews 256, no. 5-8 (March 2012): 709–21. http://dx.doi.org/10.1016/j.ccr.2011.11.011.

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Ahuja, Ishar Singh, Shailendra Tripathi, and Chhote Lal Yadava. "4-Cyanoaniline complexes with transition metal(II) halides." Transition Metal Chemistry 13, no. 2 (April 1988): 140–42. http://dx.doi.org/10.1007/bf01087806.

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Stranges, S., M. Y. Adam, M. de Simone, P. Decleva, A. Lisini, C. Cauletti, M. N. Piancastelli, and C. Furlani. "Metal oxidation state effect in photoionization of gas‐phase metal halides." Journal of Chemical Physics 102, no. 9 (March 1995): 3555–65. http://dx.doi.org/10.1063/1.468579.

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Mei, Tian-Sheng, Yue-Gang Chen, Xue-Tao Xu, Kun Zhang, Yi-Qian Li, Li-Pu Zhang, and Ping Fang. "Transition-Metal-Catalyzed Carboxylation of Organic Halides and Their Surrogates with Carbon Dioxide." Synthesis 50, no. 01 (September 13, 2017): 35–48. http://dx.doi.org/10.1055/s-0036-1590908.

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Abstract:

Carbon dioxide is not only an essential component of ‘greenhouse gases’, but also an abundant, renewable C1 feedstock in organic synthesis. The catalytic incorporation of carbon dioxide into value-added chemicals to produce carboxylic acids has received enormous attention. This review summarizes recent developments in the transition-metal-catalyzed carboxylation of organic halides and their surrogates, such as aryl, vinyl, and alkyl halides and pseudohalides.1 Introduction2 Carboxylation of Aryl Halides and Pseudohalides3 Carboxylation of Vinyl Halides and Pseudohalides4 Carboxylation of Benzyl Halides and Pseudohalides5 Carboxylation of Allyl Halides and Pseudohalides6 Carboxylation of Propargyl Halides and Pseudohalides7 Carboxylation of Alkyl Halides and Pseudohalides8 Direct Carboxylation of C–H Bonds9 Conclusions and Perspectives

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Andersson, M., J. L. Persson, and A. Rosén. "Oxidation of small transition metal clusters." Nanostructured Materials 3, no. 1-6 (January 1993): 337–44. http://dx.doi.org/10.1016/0965-9773(93)90096-t.

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Jiang, H., C. S. Petersson, and M. A. Nicolet. "Thermal oxidation of transition metal silicides." Thin Solid Films 140, no. 1 (June 1986): 115–30. http://dx.doi.org/10.1016/0040-6090(86)90166-5.

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Murata, Miki. "Transition-Metal-Catalyzed Borylation of Organic Halides with Hydroboranes." HETEROCYCLES 85, no. 8 (2012): 1795. http://dx.doi.org/10.3987/rev-12-736.

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Murata, Miki, and Yuzuru Masuda. "Transition Metal-catalyzed Silylation of Organic Halides with Hydrosilanes." Journal of Synthetic Organic Chemistry, Japan 68, no. 8 (2010): 845–53. http://dx.doi.org/10.5059/yukigoseikyokaishi.68.845.

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Roedel, Jan Nicolas, Florian Langenecker, and Ingo-Peter Lorenz. "Reactivity of 2,2-dimethylaziridine towards d10 transition metal halides." Journal of Coordination Chemistry 62, no. 11 (June 1, 2009): 1731–42. http://dx.doi.org/10.1080/00958970802715942.

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Lundgren, Rylan J., and Mark Stradiotto. "ChemInform Abstract: Transition-Metal-Catalyzed Trifluoromethylation of Aryl Halides." ChemInform 42, no. 12 (February 24, 2011): no. http://dx.doi.org/10.1002/chin.201112246.

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Thomas, J., and I. Pollini. "Ionic bonding of transition-metal halides: A spectroscopic approach." Physical Review B 32, no. 4 (August 15, 1985): 2522–32. http://dx.doi.org/10.1103/physrevb.32.2522.

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