Nickel‐Catalyzed C−N Cross‐Coupling of Primary Imines with Subsequent In Situ [2+2] Cycloaddition or Alkylation | Zendy

Power Dennis J. | Zendy; Jones Kieran D. | Zendy; Kampmann Sven S. | Zendy; Flematti Gavin R. | Zendy; Stewart Scott G. | Zendy

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Nickel‐Catalyzed C−N Cross‐Coupling of Primary Imines with Subsequent In Situ [2+2] Cycloaddition or Alkylation

Author(s) -

Power Dennis J.,

Jones Kieran D.,

Kampmann Sven S.,

Flematti Gavin R.,

Stewart Scott G.

Publication year - 2017

Publication title -

asian journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.846

H-Index - 44

eISSN - 2193-5815

pISSN - 2193-5807

DOI - 10.1002/ajoc.201700464

Subject(s) - cycloaddition , chemistry , nickel , alkylation , catalysis , reagent , in situ , primary (astronomy) , coupling reaction , combinatorial chemistry , organic chemistry , physics , astronomy

Herein, we report a new method for the C−N cross‐coupling of primary imines by using an inexpensive air‐stable nickel catalyst. This procedure allows for a subsequent in situ reaction with moisture‐sensitive reagents. In this study, we also report secondary [2+2] cycloaddition and alkylation reactions. A diverse range of substrates were explored to highlight the usefulness of this combination of reactions. The reaction products from the cycloaddition pathway, through a Staudinger reaction, have potential applications as β‐lactam antibiotics.

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