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Updated: Jun 6, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis
Xiangzhang Tao1,2,3, Wooseok Lee2,3, Zhimin Xu1
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Abstract:
We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds from readily available alkyl bistriflimides. This methodology involves the assembly of two leaving groups on alkyl amines to form alkyl bistriflimides, followed by their effective coupling with a wide range of alkyl halides, alkyl pseudohalides, aryl halides, and alkenyl halides under electrochemical reductive conditions. Moreover, the successful application of electrochemical reductive relay cross-coupling and transition metal-free cross-electrophile coupling further demonstrates the versatility of alkyl bistriflimides as valuable building blocks in organic synthesis. Combined control experiments and density functional theory calculations provide insights into the reaction pathway and the crucial role of iodide in the catalytic process.
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