Nickel-Catalyzed C-N Cross-Coupling of Primary Imines with Subsequent InSitu [2+2] Cycloaddition or Alkylation

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 insitu reaction with moisture-sensitive reagents. In this study, we also report secondary [2+2] cycloaddition and alkylation reaction...

Full description

Saved in:
Bibliographic Details
Published in:Asian journal of organic chemistry 2017-12, Vol.6 (12), p.1794
Main Authors: Power, Dennis J, Jones, Kieran D, Kampmann, Sven S, Flematti, Gavin R, Stewart, Scott G
Format: Article
Language:English
Subjects:
Alkylation
Amides
Antibiotics
Cross coupling
Cycloaddition
Imines
Nickel
Organic chemistry
Reaction products
Reagents
Substrates
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 insitu 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 [beta]-lactam antibiotics.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700464