Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions

Recent progress in the oxidative cross-coupling between two nucleophiles (Nu1/Nu2) is reported. Lipshutz and co-workers reported the first oxidative crosscoupling reaction between two different aryl metal reagents to form unsymmetrical biaryls in the presence of stoichiometric amounts of CuCN with oxygen as the oxidant at low temperature. One catalytic procedure based on the oxidative coupling between two alkyl metal reagents was demonstrated by Lei and Zhang, in which the homocouplings of benzylic zinc reagents were investigated in the presence of a palladium catalyst. The first report about the oxidative cross-coupling of terminal alkynes with alkanes was demonstrated by Miura and co-workers, in which the sp3 carbon of alkane was adjacent to a tertiary amine. Zhang and co-workers developed a one-pot approach to C3-position acetoxylated biindolyls realized via palladium catalysis by the use of AgOAc under oxygen atmosphere as oxidants.