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Updated: Sep 27, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Sequential olefination-dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard
Lei Yu1, Guo-Qiao Lai1, Pinglu Zhang1
1Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry, and Chemical Engineering, Hangzhou Normal University Hangzhou 311121 China laiguoqiao@aliyun.com zeli@hznu.edu.cn.
Abstract:
Products of main group elements from cross-coupling reactions have been shown to serve as Lewis acids, mediating further reactions of organic coupling products. Thus, the nickel-catalysed olefination of benzylic dithioacetal with MeMgI in benzene in a sealed Schlenk tube at 130 °C generates magnesium mercaptide which regioselectively converts 2-arylpropene into a dimer in good yield. Aryl iodide reacts with 2-propenylmagnesium bromide in the presence of 1,2-ethanedithiol and NiCl2(PPh3)2 to yield the same dimer. Replacement of the Grignard reagent by an organozinc reagent gives the dimers in a better yield.
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