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“Golden Age” of Homogeneous Catalytic Chemistry of Alkynes: Some Oxidative Transformations of Alkynes (A Review)

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Abstract

Methods for carrying out coupling reactions in the chemistry of alkynes to form C–C bonds (oxidative dehydrocondensation reactions, Cadiot–Chodkiewicz reaction, and Sonogashira reaction) are analyzed and generalized. Protocols of synthesis of products of these reactions are also presented, including homogeneous and heterogeneous catalytic systems. In all cases, emphasis is placed on the kinetics and mechanisms of reactions with the discussion of the results of kinetic and spectrometric studies of the mechanisms of coupling reactions involving Cu(I, II, III), Au(I, III), Pd(0, I, II), and Fe (0, I, II, III) complexes. Particular attention is paid to the heterogeneous catalysis of oxidation reactions of alkynes with the participation of nanoparticles and nanoclusters of Pd, Au, Ag, and other metals. The nature of the intermediates containing these metals and the relationships between various oxidative and nonoxidative transformations of alkynes are discussed.

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ACKNOWLEDGMENTS

I thank K. Egiazaryan, graduate student, Chair of Physical Chemistry, MIREA—Russian Technological University, Moscow, Russia, for his invaluable help in preparing this review; Dr. L.G. Fedenok for very useful discussions concerning the mechanisms of the OD reaction; Professor O.L. Kalija and Professor L.G. Bruk for valuable advice on the content and structure of the review.

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No support was received for the preparation of this review.

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  1. Lomonosov Institute of Fine Chemical Technologies, MIREA—Russian Technological University, 119571, Moscow, Russia

    O. N. Temkin

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Translated by V. Glyanchenko

Abbreviations and notation: EDA, ethylenediamine; TMEDA, tetramethylethylenediamine; THF, tetrahydrofuran; MA, methylacetylene; DMDA, dimethyldiacetylene; CMA, chloromethylacetylene; DA, diacetylene; MDA, methyldiacetylene; DCE, dichloroethylene; PEG, polyethylene glycol; BMA, bromomethylacetylene; CMA, copper methylacetylide; TBA, tetrabutylamine; DMF, dimethylformamide; EG, ethylene glycol; Py, pyridine; PiPy, piperidine; DiPy, dipyridyl; AN, acetonitrile; Phen, phenanthrene; BMIM, butylmethylimidazole; dba, dibenzylideneacetone; hal, halides; dppm, 1,2-bis(diphenylphosphino)methane; dppp, 1,2-bis(diphenylphosphino)propane; dppe, 1,2-bis(diphenylphosphino)ethane; dppf, 1,1-bis(diphenylphosphino)ferrocene; BINAP, bis(naphthyldiphenylphosphine); Xantophos, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene; TEMPO, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl; TMEDA, tetramethylethylenediamine; TMED, tetramethylethylenediamine; DME, dimethyl ether; DMED, dimethylethylenediamine; NMP, N-methyl-2-pyrrolidone; dipy, dipyridyl; NHC, N-heterocyclic carbene; HX, acids; D, optical density; POCC, polyfunctional oxygen-containing compounds; NMR, nuclear magnetic resonance; OS, oxidation state; ORR, redox reactions; OD, oxidative dehydrocondensation of alkynes (coupling); B, base; NC, nanocluster; NP, nanoparticle; OA, oxidative addition; TM, transmetalation; RE, reductive elimination; rt, room temperature; TOF, turnover frequency of catalyst; TON, turnover number of catalyst; EDG, electron donating group; EWG, electron withdrawing group; KIE, kinetic isotope effect; IL, ionic liquids; RDS, rate-determining step; TPR, temperature-programmed reaction; CSI-MS, cold-spray ionization mass spectrometry; STM, scanning tunneling microscopy; ESI-MS, electrospray ionization mass spectrometry; CID, collision-induced dissociation; XPS, X-ray photoelectron spectroscopy; HR TEM, high-resolution transmission electron microscopy, FE SEM, field emission scanning electron microscopy; STM, scanning tunneling microscopy; DFT, density functional theory; XRD, X-ray powder diffraction analysis; and ICP-ES, inductively coupled plasma emission spectroscopy.

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Temkin, O.N. “Golden Age” of Homogeneous Catalytic Chemistry of Alkynes: Some Oxidative Transformations of Alkynes (A Review). Kinet Catal 64, 521–577 (2023). https://doi.org/10.1134/S0023158423050117

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