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Photoinduced C(sp 3 )−N Bond Cleavage Leading to the Stereoselective Syntheses of Alkenes
Author(s) -
Yang ZeKun,
Xu NingXin,
Wang Chao,
Uchiyama Masanobu
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900886
Subject(s) - alkene , chemistry , alkyl , bond cleavage , photochemistry , stereoselectivity , photoredox catalysis , catalysis , selectivity , cleavage (geology) , medicinal chemistry , organic chemistry , photocatalysis , materials science , fracture (geology) , composite material
Herein we report a versatile Mizoroki–Heck‐type photoinduced C(sp 3 )−N bond cleavage reaction. Under visible‐light irradiation (455 nm, blue LEDs) at room temperature, alkyl Katritzky salts react smoothly with alkenes in a 1:1 molar ratio in the presence of 1.0 mol % of commercially available photoredox catalyst without the need for any base, affording the corresponding alkyl‐substituted alkenes in good yields with broad functional‐group compatibility. Notably, the E / Z ‐selectivity of the alkene products can be controlled by an appropriate choice of photoredox catalyst.