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Nickel-Catalyzed 1,2-Diarylation Of Alkenyl Carboxylates: A Gateway To 1,2,3-Trifunctionalized Building Blocks.

Joseph Derosa, Taeho Kang, Văn Thụy Trần, Steven R Wisniewski, Malkanthi K Karunananda, Tanner C. Jankins, Kane L. Xu, Keary M. Engle
Published 2019 · Medicine, Chemistry
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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 group.
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