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

preprint
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.

Funding

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

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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