Directed nickel-catalyzed negishi cross coupling of alkyl aziridines

Daniel K. Nielsen; Chung Yang Huang; Abigail G. Doyle

doi:10.1021/ja4076716

Directed nickel-catalyzed negishi cross coupling of alkyl aziridines

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

Research output: Contribution to journal › Article › peer-review

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Abstract

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.

Original language	English (US)
Pages (from-to)	13605-13609
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	135
Issue number	36
DOIs	https://doi.org/10.1021/ja4076716
State	Published - Sep 11 2013

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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abstract = "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.",

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AU - Huang, Chung Yang

AU - Doyle, Abigail G.

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N2 - 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.

AB - 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.

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Directed nickel-catalyzed negishi cross coupling of alkyl aziridines

Abstract

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