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Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis

Year: 2024
Type: article
Abstract: Alcohols are among the most abundant chemical feedstocks, yet they remain vastly underutilized as coupling partners in transition metal catalysis. Herein, we describe a copper metallaphotoredox manifold for the open shell deoxygenative coupling of alcohols with N -nucleophiles to forge C( sp 3 )–N bonds, a linkage of high value in pharmaceutical agents that is challenging to access via conventional cross-coupling techniques. N -heterocyclic carbene (NHC)-mediated conversion of alcohols into the corresponding alkyl radicals followed by copper-catalyzed C–N coupling renders this platform successful for a broad range of structurally unbiased alcohols and 18 classes of N -nucleophiles.
DOI: 10.1021/jacs.4c04477
Authors: William P. Carson, Artem V. Tsymbal, Robert W. Pipal, Grant A. Edwards, Joseph R. Martinelli, Albert Cabré, David W. C. MacMillan
Language: English
Field: Chemistry
Open Access status: green
Funders: National Science Foundation, Bristol-Myers Squibb, Eli Lilly and Company, Pfizer, Merck, Princeton University, National Institutes of Health, Genentech, National Institute of General Medical Sciences, Division of Graduate Education, Janssen Pharmaceuticals, Genmab
OpenAlex ID: W4399177809
FWCI: 8.799
Cites: 47
Cited by: 61
Related to: 10