Published in:
European Journal of Organic Chemistry, 2014 (2014) 33, Seite 7347-7352
Language:
English
DOI:
10.1002/ejoc.201403021
ISSN:
1434-193X;
1099-0690
Origination:
Footnote:
Description:
AbstractAn 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.