Open AccessA Chemoselective and Scalable Transfer Hydrogenation of Aryl Imines by Rapid Continuous Flow Photoredox Catalysis
Author(s) -
Rowan Pilkington,
Nikolai Piers Rossouw,
Dean J van As,
Anastasios Polyzos
Publication year - 2019
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.2019.823
Subject(s) - transfer hydrogenation , photoredox catalysis , chemistry , ketone , aryl , continuous flow , catalysis , amine gas treating , combinatorial chemistry , flow chemistry , chemoselectivity , aryl halide , functional group , halide , organic chemistry , photocatalysis , palladium , alkyl , physics , polymer , ruthenium , mechanics
The chemoselective reduction of diaryl imines in the presence of competitively reducible groups is uniquely accessed through precise control of reaction and irradiation time by continuous flow visible light photoredox catalysis. The method enables the mild and efficient transfer hydrogenation of diaryl imines in the presence of sensitive functionality including halides, ester, ketone, and cyano groups. The flow protocol is efficient, rapid (>98% conversion within 9 min) and readily scaled to deliver multigram quantities of amine products in high purity.