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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.