4 years ago

Photoredox-Controlled Mono- and Di-Multifluoroarylation of C(sp3)−H Bonds with Aryl Fluorides

Photoredox-Controlled Mono- and Di-Multifluoroarylation of C(sp3)−H Bonds with Aryl Fluorides
Jin Xie, Matthias Rudolph, A. Stephen K. Hashmi, Frank Rominger
A controllable mono- and di-multifluoroarylation of acyclic and cyclic N-aryl amines with aryl fluorides by photocatalyzed dual C(sp3)−H/C(sp2)−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(sp3)−C(sp2) 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(sp3)−H bonds with aryl fluorides. A broad range of valuable α-fluoroarylated amines were obtained by the controlled mono- and di-multifluoroarylation of N-aryl amines with aryl fluorides by photocatalytic C(sp3)−H/C(sp2)−F functionalization. A one-pot variant also provides access to unsymmetrically disubstituted products.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700135

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