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Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines

2013; American Chemical Society; Volume: 135; Issue: 36 Linguagem: Inglês

10.1021/ja4076716

1943-2984

Daniel K. Nielsen, Chung‐Yang Huang, Abigail G. Doyle,

Catalytic Cross-Coupling Reactions

Herein we report a nickel-catalyzed C–C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp3–N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn) bearing an electron-deficient olefin that directs oxidative addition and facilitates reductive elimination. Studies pertinent to elucidation of the mechanism of cross coupling are also presented.