Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis
William Carson, Artem V. Tsymbal, Robert W. Pipal, Grant A. Edwards, Joseph R. Martinelli, Albert Cabré, David W. C. MacMillan
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.