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

Jianzhong Liu; Xiaojin Wen; Chong Qin; Xinyao Li; Xiao Luo; Ao Sun; Bencong Zhu; Song Song; Ning Jiao

doi:10.1002/anie.201705671

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

Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11940-11944. doi: 10.1002/anie.201705671. Epub 2017 Aug 18.

Authors

Jianzhong Liu¹, Xiaojin Wen¹, Chong Qin¹, Xinyao Li¹, Xiao Luo¹, Ao Sun¹, Bencong Zhu¹, Song Song¹, Ning Jiao^{1

2}

Affiliations

¹ State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191, China.
² State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

PMID: 28734100
DOI: 10.1002/anie.201705671

Abstract

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.

Keywords: C−C bond cleavage; alkenes; hydrocarbons; oxygenation; sigmatropic rearrangement.

Publication types

Research Support, Non-U.S. Gov't