Palladium-catalyzed Heck cyclization/allylation with homoallyl alcohols via retro-allylation

Ping-Xin Zhou; Xiaozhe Yang; Xueyan Du; Shujie Zhao; Han Wang; Xinguang Li; Ning Liu; Xinqiang Tan; Feng Ren; Yong-Min Liang

doi:10.1039/D2QO00655C

Palladium-catalyzed Heck cyclization/allylation with homoallyl alcohols via retro-allylation†

Ping-Xin Zhou,

*^a Xiaozhe Yang,^a Xueyan Du,^a Shujie Zhao,^a Han Wang,^a Xinguang Li,^a Ning Liu,^a Xinqiang Tan,*^a Feng Ren*^ab and Yong-Min Liang

^c

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* Corresponding authors

^a School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang, China
E-mail: zhoupingxin518@y163.com, tanxq@xxmu.edu.cn, 1215377283@qq.com

^b Henan International Joint Laboratory of Immunity and Targeted Therapy for liver-intestinal Tumors, Xinxiang Medical University, Xinxiang, China

^c State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China

Abstract

A palladium-catalyzed reaction of aryl iodide-tethered alkenes with homoallyl alcohols is reported, providing a convenient and efficient approach to C(sp³)–allylation products. The cascade process involves intramolecular Heck/retro-allylation. This new approach has good functional group compatibility, broad substrate scope and high efficiency. This domino reaction further proved that homoallyl alcohols are convenient and efficient allylation sources.

Organic Chemistry Frontiers

Palladium-catalyzed Heck cyclization/allylation with homoallyl alcohols via retro-allylation†

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Palladium-catalyzed Heck cyclization/allylation with homoallyl alcohols via retro-allylation

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