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Photodriven Transfer Hydrogenation of Olefins
Author(s) -
Leow Dasheng,
Chen YingHo,
Hung TzuHang,
Su Ying,
Lin YiZhen
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403021
Subject(s) - diimide , chemistry , isomerization , hydrazine (antidepressant) , photochemistry , catalysis , inert gas , hydrogen , organic chemistry , polymer chemistry , molecule , perylene , chromatography
An improved practical method for the photodriven diimide reduction of olefins was investigated. This catalyst‐free procedure proceeds at ambient temperature, utilizes air as oxidant and a lower hydrazine loading, and produces inert nitrogen gas as the sole byproduct. Several functional groups were tolerated, and in some cases, the reaction was chemoselective. Challenging substrates such as cinnamate ester derivatives and trans ‐stilbene were reduced in excellent yields. The small amount of UVA rays emitted from a household compact fluorescent light bulb was proposed to enable the cis / trans isomerization of the diimide and to promote the loss of hydrogen from the diimide.