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Photoredox‐Controlled Mono‐ and Di‐Multifluoroarylation of C(sp 3 )−H Bonds with Aryl Fluorides
Author(s) -
Xie Jin,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700135
Subject(s) - aryl , regioselectivity , surface modification , chemistry , combinatorial chemistry , medicinal chemistry , catalysis , organic chemistry , alkyl
A controllable mono‐ and di‐multifluoroarylation of acyclic and cyclic N ‐aryl amines with aryl fluorides by photocatalyzed dual C(sp 3 )−H/C(sp 2 )−F functionalization has been developed, providing new access to a wide array of valuable α‐fluoroarylated amines. In addition, the one‐pot consecutive hetero‐di‐multifluoroarylation of N ‐aryl pyrrolidines and N , N ‐dimethylanilines was achieved with high to excellent diastereoselectivity. This new defluorinative C(sp 3 )−C(sp 2 ) coupling is distinguished by a broad scope, good regioselectivity, and mild conditions as well as gram‐scale and late‐stage applicability, and thus constitutes a significant advance in the arylation of unactivated C(sp 3 )−H bonds with aryl fluorides.