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Oxygenation of Simple Olefins through Selective Allylic C−C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Author(s) -
Liu Jianzhong,
Wen Xiaojin,
Qin Chong,
Li Xinyao,
Luo Xiao,
Sun Ao,
Zhu Bencong,
Song Song,
Jiao Ning
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705671
Subject(s) - chemistry , allylic rearrangement , alkyl , bond cleavage , reagent , aryl , stereoselectivity , azide , cinnamyl alcohol , cleavage (geology) , organic chemistry , medicinal chemistry , catalysis , cinnamaldehyde , geotechnical engineering , fracture (geology) , engineering
A novel metal‐free allylic C−C σ‐bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2‐Aryl or alkyl migration through allylic C−C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O‐atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal‐free conditions, and high regio‐ and stereoselectivity.