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Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with N , N′ ‐Dimethylpropylene Urea as H ‐Donor
Author(s) -
Cai SaiHu,
Wang DingXing,
Ye Lu,
Liu ZeYao,
Feng Chao,
Loh TeckPeng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700937
Subject(s) - chemistry , pyrroline , intramolecular force , urea , catalysis , photochemistry , visible spectrum , photoredox catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry , photocatalysis , physics , optoelectronics
Synthesis of 3,4‐pyrroline derivatives via visible‐light‐induced hydro/oxyimination of unactivated olefins is reported. In the presence of the photoredox catalyst fac ‐Ir(ppy) 3 , the key iminyl radical intermediate can be readily generated from O ‐acyl oximes, and undergoes intramolecular cyclization and H ‐abstraction from solvent or is trapped by TEMPO to give the corresponding hydro/oxyimination product, respectively. Mechanistic investigations indicate that N,N′ ‐dimethylpropylene urea (DMPU) works as both reducing agent for catalyst regeneration and H ‐donor for product formation in this process.