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Updated: Apr 15, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ni(II)/BINOL-catalyzed alkenylation of unactivated C(sp(3))-H bonds
Yue-Jin Liu1, Zhuo-Zhuo Zhang, Sheng-Yi Yan
1Department of Chemistry, Zhejiang University, Hangzhou 310027, China. bfshi@zju.edu.cn.
Abstract:
The first nickel-catalyzed alkenylation of unactivated C(sp(3))-H bonds with vinyl iodides is described. The catalytic system comprises an inexpensive and air-stable Ni(acac)2 as the catalyst and BINOL as the ligand, which is highly efficient for the alkenylation of β-methyl C(sp(3))-H bonds of a broad range of aliphatic carboxamides. The resulting olefins can serve as versatile handles for further preparation. Additionally, we also demonstrated the synthesis of functionalized carboxamides bearing α-quaternary carbon centers from simple pivalamide via nickel-catalyzed sequential C(sp(3))-H bond functionalization.
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