Photoredox-controlled mono- and di-multifluoroarylation of C(sp3)-H bonds with aryl fluorides

• Verfasst von: Xie, Jin [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Photoredox-controlled mono- and di-multifluoroarylation of C(sp3)-H bonds with aryl fluorides
• Verf.angabe: Jin Xie, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
• Umfang: 5 S.
• Fussnoten: Im Titel ist die Zahl 3 als Hochzahl dargestellt ; Gesehen am 23.08.2017
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Jahr Quelle: 2017
• Band/Heft Quelle: 56(2017), 25, S. 7266-7270
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201700135
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1562648888

Abstract

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.