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

• DOI: 10.1002/ange.201913062
• Publication Date: 2019-11-06T10:24:03Z
• Authors: Joseph Derosa; Taeho Kang; Van T. Tran; Steven R. Wisniewski; Malkanthi K. Karu...; Tanner C. Jankins; Kane L. Xu; Keary M. Engle
• Keywords: Alkene; Stereocenter; Carboxylate

Abstract 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 1,2‐arylalkenylated products with excellent regiocontrol. To demonstrate synthetic utility method, a representative product prepared on gram scale then diversified to eight 1,2,3‐trifunctionalized building blocks using two‐electron one‐electron logic. Using this three routes toward bioactive molecules are improved in terms yield and/or step count. This method represents first example catalytic 1,2‐diarylation an alkene directed by native carboxylate group.