Nickel/Photoredox Dual-Catalyzed Regiodivergent Aminoalkylation of Unactivated Alkyl Halides

A mild and regiodivergent aminoalkylation of unactivated alkyl halides is disclosed via a dual photoredox/nickel catalysis. Bipyridyl-type ligands without an ortho-substituent control the site-selective coupling at the original position, while ortho-disubstituted ligands tune the site-selectivity at...

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Published in:Journal of the American Chemical Society 2023-10, Vol.145 (42), p.23385-23394
Main Authors: Wang, Wenlong, Yan, Xueyuan, Ye, Fu, Zheng, Songlin, Huang, Genping, Yuan, Weiming
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Language:English
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cited_by cdi_FETCH-LOGICAL-a301t-6aee45ff61a41163964404cea8a503830688be9d4dab6300c929262efcf50b313
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container_issue 42
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container_title Journal of the American Chemical Society
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creator Wang, Wenlong
Yan, Xueyuan
Ye, Fu
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Yuan, Weiming
description A mild and regiodivergent aminoalkylation of unactivated alkyl halides is disclosed via a dual photoredox/nickel catalysis. Bipyridyl-type ligands without an ortho-substituent control the site-selective coupling at the original position, while ortho-disubstituted ligands tune the site-selectivity at a remote, unprefunctionalized position. Mechanistic studies combined with DFT calculations give insight into the mechanism and the origins of the ligand-controlled regioselectivity. Notably, this redox-neutral, regiodivergent alkyl–alkyl coupling features mild conditions, broad substrate scope for both alkyl coupling partners, and excellent site-selectivity and offers a straightforward way for α-alkylation of tertiary amines to synthesize structurally diverse alkylamines and value-added amino acid derivatives.
doi_str_mv 10.1021/jacs.3c09705
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title Nickel/Photoredox Dual-Catalyzed Regiodivergent Aminoalkylation of Unactivated Alkyl Halides
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