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Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks

submitted on 25.09.2019, 08:09 and posted on 27.09.2019, 20:28 by Joseph Derosa, Taeho Kang, Van Tran, Steven Wisniewski, Malkanthi Karunananda, Tanner Jankins, Kane Xu, Keary Engle
A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate functional group.


Bristol Myers-Squibb (Unrestricted Grant)

National Science Foundation (CHE-1800280)

Alfred P. Sloan Fellowship Program

Camille Dreyfus Teacher-Scholar Program

National Science Foundation (DGE-1346837)

Kwanjeong Educational Foundation

Dr. Art Olson and Shirley King


Email Address of Submitting Author


The Scripps Research Institute



ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest to declare.