Transition-metal catalyzed oxidative cross-coupling reactions to form C–C bonds involving organometallic reagents as nucleophiles

Abstract

Transition-metal-catalyzed coupling reactions have become a versatile tool for chemical bond formation. From the variation of the coupling partners, coupling reactions can be classified into three models: traditional coupling, reductive coupling and oxidative coupling. The oxidative coupling, which is different from the traditional coupling, occurs between two nucleophiles. This critical review focuses on transition-metal-catalyzed oxidative coupling reactions involving organometallic reagents as nucleophiles. Since the scope of the oxidative coupling is highly diversified, this paper only reviews the oxidative coupling reactions concerning C-C bond formation, including the coupling between organometal reagents and hydrocarbons as well as coupling between two organometal reagents. Since terminal alkynes are normally activated by metal salts and in situ form the alkynyl metal reagents in coupling reactions, they are directly considered as organometal reagents in this review. Intramolecular oxidative couplings and oxidative cyclizations are not included in this critical review. Moreover, there are many examples of oxidative coupling leading to the formation of functional materials, such as the oxidative polymerization of thiophenes. Since several reviews in these areas have been published they are not included in this review either (99 references).

Revealing the halide effect on the kinetics of the aerobic oxidation of Cu(i) to Cu(ii)

“…[1][2][3][4][5][6] However, the high activation energy of molecular oxygen usually requires a transition metal catalyst. 7 Besides the traditionally used precious Pd catalysts, Cu catalysts have received considerable attention during last decades.…”

“…The detail kinetic profiles were recorded by in situ IR 2 | J. Name., 2012, 00, [1][2][3] This journal is © The Royal Society of Chemistry 2012 ( Fig. 1), in which the utilization of CuCl as the pre-catalyst afforded the highest reaction rate.…”

Copper-catalyzed oxidative coupling of carboxylic acids with formamides for the synthesis of α,β-unsaturated amides

“…5 Transition-metal-catalyzed coupling reactions including cross dehydrogenative coupling or oxidative coupling have become a versatile tool for chemical bonds formation. 6 Our group have gained many achievements in this field as well. 7 As we know, carboxylic acid is a kind of ubiquitous compound in nature and organic chemistry.…”

Advances in Copper‐Catalyzed CC Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds

“…[1][2][3] Among the various methods for CÀC coupling, cross-coupling reactions that use aryl/vinyl halides as C-electrophile partners are the most-practical. [1][2][3] Among the various methods for CÀC coupling, cross-coupling reactions that use aryl/vinyl halides as C-electrophile partners are the most-practical.…”