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Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross-Coupling

Chung-Yang (Dennis) Huang and Abigail G. Doyle*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: agdoyleprinceton.edu

C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2015, 137, 5638-5641.

DOI: 10.1021/jacs.5b02503 (free Supporting Information)


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Abstract

A Ni-catalyzed Negishi cross-coupling with 1,1-disubstituted styrenyl aziridines delivers valuable β-substituted phenethylamines via a challenging reductive elimination that affords a quaternary carbon. An electron-deficient olefin ligand is crucial for achieving high rates and chemoselectivity for C-C bond formation over β-H elimination.

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Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines

C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2012, 134, 9541-9544.


Key Words

β-substituted amines


ID: J48-Y2015