Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with  N , N′ ‐Dimethylpropylene Urea as  H ‐Donor | Zendy

Cai SaiHu | Zendy; Wang DingXing | Zendy; Ye Lu | Zendy; Liu ZeYao | Zendy; Feng Chao | Zendy; Loh TeckPeng | Zendy

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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.

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