Methods and Mechanisms for Cross-Electrophile Coupling of Csp 2 Halides with Alkyl Electrophiles

Cross-electrophile coupling, the cross-coupling of two different electrophiles, avoids the need for preformed carbon nucleophiles, but development of general methods has lagged behind cross-coupling and C-H functionalization. A central reason for this slow development is the challenge of selectively coupling two substrates that are alike in reactivity. This Account describes the discovery of generally cross-selective reactions of aryl halides and acyl halides with alkyl halides, the mechanistic studies that illuminated the underlying principles of these reactions, and the use of these fundamental principles in the rational design of new cross-electrophile coupling reactions. Although the coupling of two…

• UO
  University of Rochester
• AC
  American Chemical Society Petroleum Research Fund
• NI
  National Institute of General Medical Sciences

  Award: R01 GM097243