Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines

25 May 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


A Ni-catalyzed reductive cross-coupling of heteroaryl imines with C(sp3) electrophiles for the preparation of heterobenzylic amines is reported. This umpolung-type alkylation proceeds under mild conditions, avoids the pre-generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox-active ligand upon coordination to a low-valent Ni center. The resulting bis(2-imino)heterocycle·Ni complexes can engage in alkylation reactions with a variety of C(sp3) electrophiles, giving heterobenzylic amine products in good yields.


non-innocent ligand
imine alkylation
heterobenzylic amines

Supplementary materials

Supporting Information
Experimental procedures, characterization data, computational details


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