Solvent-Controlled, Tunable β-OAc and β-H Elimination in Rh(III)-Catalyzed Allyl Acetate and Aryl Amide Coupling via C–H Activation

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• 作者：Huimin Dai ; Chao Yu ; Zihao Wang ; Hong Yan ; Changsheng Lu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：18
• 期：14
• 页码：3410-3413
• 全文大小：347K
• 年卷期：0
• ISSN：1523-7052

文摘

The Heck reaction between arenes and allyl acetate has led to cinnamyl derivatives and allyl products depending on the regioselectivity of β-elimination. The regioselectivity can be controlled by the solvent in the Rh(III)-catalyzed arene–allyl acetate coupling via C–H activation: (1) in THF, cinnamyl derivatives via β-H elimination were generated; (2) in MeOH, allyl products via β-OAc elimination were produced. Both routes have advantages such as excellent γ-selectivity toward allyl acetate, good to excellent yields, and broad substrate scope.