Oxygenation of Simple Olefins through Selective Allylic C−C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Jianzhong Liu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorXiaojin Wen
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorChong Qin
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorXinyao Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorXiao Luo
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorAo Sun
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorBencong Zhu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorCorresponding Author
Dr. Song Song
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorCorresponding Author
Prof. Ning Jiao
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorJianzhong Liu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorXiaojin Wen
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorChong Qin
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorXinyao Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorXiao Luo
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorAo Sun
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorBencong Zhu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorCorresponding Author
Dr. Song Song
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
Search for more papers by this authorCorresponding Author
Prof. Ning Jiao
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd. 38, Beijing, 100191 China
State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorGraphical Abstract
Cut and paste: A novel metal-free allylic C−C bond cleavage of simple unfunctionalized olefins was developed for the synthesis of valuable cinnamyl aldehyde derivatives with high regio- and stereoselectivity. This method not only provides a new approach to cinnamyl aldehydes, but also expands the application of alkyl azides as well as the recombination of olefins in organic synthesis.
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.
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