Radical-Mediated Heck-Type Alkylation: Stereoconvergent Synthesis of Functionalized Polyenes

Hong Zhang^†, Xinxin Wu^†, Yunlong Wei,^† and Chen Zhu^*,†,‡（朱晨）

^† Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China

^‡ Key Laboratory of Synthesis Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, China

Org. Lett. 2019, 21, 7568--7572

The stereospecific synthesis of polyenes is of great synthetic value. Disclosed herein is a new, efficient, stereoconvergent approach for the synthesis of functionalized polyenes via a radical-mediated Heck-type alkylation. The easily accessed Z- and E-mixed alkenes are harnessed as starting material, leading to a unique stereoisomer of polyenes. In addition, the transformation features mild reaction conditions and broad functional group compatibility. A variety of valuable 1,3-dienes and 1,3,5-trienes are afforded in useful yields.

链接：https://pubs.acs.org/doi/abs/10.1021/acs.orglett.9b02838