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Direct Aldehyde C–H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis

Author:
Zhang, Xiaheng, MacMillan, David W. C.
Source:
Journal of the American Chemical Society 2017 v.139 no.33 pp. 11353-11356
ISSN:
1520-5126
Subject:
aldehydes, alkylation, arylation, carbon-hydrogen bond activation, catalytic activity, haloperidol, hydrogen, nickel, organobromine compounds, protocols, redox reactions
Abstract:
A mechanism that enables direct aldehyde C–H functionalization has been achieved via the synergistic merger of photoredox, nickel, and hydrogen atom transfer catalysis. This mild, operationally simple protocol transforms a wide variety of commercially available aldehydes, along with aryl or alkyl bromides, into the corresponding ketones in excellent yield. This C–H abstraction coupling technology has been successfully applied to the expedient synthesis of the medicinal agent haloperidol.
Agid:
5795754