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

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Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States
Cite this: J. Am. Chem. Soc. 2017, 139, 15, 5313–5316
Publication Date (Web):March 30, 2017
Copyright © 2017 American Chemical Society

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    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.

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