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Updated: Jan 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

アルコールとアルケンによる直接α-C-Hアルキル化

Lilan Duan¹, Yutao Shi¹, Xiaochen Ji¹

¹Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.

Organic letters

|December 19, 2025

Abstract:

Herein, we report a direct α-C-H alkylation of alcohols with alkenes enabled by organic photoredox catalysis, in which the additive trimethylsilyl azide (TMSN₃) plays a crucial role in the selective activation of the α-C-H bond of free alcohols. Both α-CF₃-alkenes and acrylamides showed high efficiency and excellent chemoselectivity in this transformation, affording various γ-trifluoromethyl alcohols and γ-hydroxyl amides under mild conditions. The late-stage modification of several drug derivatives was achieved, and the synthetic utility of this protocol was further highlighted by the scaled-up reaction and several derivations of the products.

キーワード:

光レドックス触媒 C-Hアルキル化アルコールアルケン有機合成トリメチルシリルアジド

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