Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C–N Bond Activation

We developed a strategy to harness alkyl amines as alkylating agents via C–N bond activation. This Suzuki–Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C–N bond activation of an amine with an unactiva...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-04, Vol.139 (15), p.5313-5316
Main Authors: Basch, Corey H, Liao, Jennie, Xu, Jianyu, Piane, Jacob J, Watson, Mary P
Format: Article
Language:English
Subjects:
Amines - chemical synthesis
Amines - chemistry
Catalysis
Molecular Structure
Nickel - chemistry
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Summary:We developed a strategy to harness alkyl amines as alkylating agents via C–N bond activation. This Suzuki–Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C–N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a NiI/NiIII catalytic cycle.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b02389