TY - JOUR
T1 - Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis
T2 - Sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides
AU - Zhang, Xiaheng
AU - MacMillan, David W.C.
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/10/26
Y1 - 2016/10/26
N2 - Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.
AB - Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.
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U2 - 10.1021/jacs.6b09533
DO - 10.1021/jacs.6b09533
M3 - Article
C2 - 27718570
AN - SCOPUS:84992743753
SN - 0002-7863
VL - 138
SP - 13862
EP - 13865
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 42
ER -