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Journal of the American Chemical Society

Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling.


PMID 25879801

Abstract

A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines has been developed. This method delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. A novel electron-deficient olefin ligand, Fro-DO, proved crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination. This ligand is easy to access, is stable, and presents a modular framework for reaction discovery and optimization. We expect that these attributes, combined with the fact that the ligands impart distinct electronic properties to a metal, will support the invention of new transformations not previously possible using established ligands.

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804371
Fro-DO, mixture of diastereomers, 97%
C24H22N2O6S2