Photoredox‐Controlled Mono‐ and Di‐Multifluoroarylation of C(sp 3 )−H Bonds with Aryl Fluorides | Zendy

Xie Jin | Zendy; Rudolph Matthias | Zendy; Rominger Frank | Zendy; Hashmi A. Stephen K. | Zendy

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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.

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