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Sulfonamide Directivity Enables Ni-Catalyzed 1,2-Diarylation of Diverse Alkenyl Amines

preprint
submitted on 10.07.2020 and posted on 13.07.2020 by Omar Apolinar, Van Tran, Michael A. Schmidt, Joseph Derosa, Keary Engle
1,2-Diarylation of alkenyl sulfonamides with aryl iodides and aryl boronic esters under nickel catalysis is reported. The developed method tolerates coupling partners with disparate electronic properties and substitution patterns. 1,2- and 1,1-Disubstituted alkenes, as well as alkenes distal from the directing group, are all accommodated. Control experiments are consistent with a N–Ni coordination mode of the directing group, which stands in contrast to earlier reports on amide-directed 1,2-diarylation that involve carbonyl coordination. The synthetic utility of the method arises from the dual function of the sulfonamide as both a directing group and masked amine nucleophile. This is highlighted by various product diversifications where complex amine compounds are synthesized in a two-step sequence of N-functionalization and deprotection of the sulfonyl group.

Funding

NSF-CHE-1800280

NSF-DGE-1346837

NSF-DGE-1842471

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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