Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes

DOI: 10.1002/anie.201705671

Source and publish data:

Angewandte Chemie - International Edition p. 11940 - 11944 (2017)

Update date:2022-08-03

Topics:

Authors:

Liu, Jianzhong

Wen, Xiaojin

Qin, Chong

Li, Xinyao

Luo, Xiao

Sun, Ao Sun, Ao

Zhu, Bencong

Song, Song

Jiao, Ning

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Article abstract of DOI:10.1002/anie.201705671

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.

Full text of DOI:10.1002/anie.201705671

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