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Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines

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., 2012, 134, 9541-9544.

DOI: 10.1021/ja3013825 (free Supporting Information)



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Abstract

A cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is possible under mild and functional-group-tolerant conditions in the presence of inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand to yield β-substituted amines. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C bond formation.

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

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


Key Words

β-substituted amines, Negishi Coupling


ID: J48-Y2012-1850