Copper(I)-Catalyzed Allylic Substitutions with a Hydride Nucleophile

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• 作者：T. N. Thanh Nguyen ; Niklas O. Thiel ; Felix Pape ; Johannes F. Teichert
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：18
• 期：10
• 页码：2455-2458
• 全文大小：341K
• 年卷期：0
• ISSN：1523-7052

文摘

An easily accessible copper(I)/N-heterocyclic carbene (NHC) complex enables a regioselective hydride transfer to allylic bromides, an allylic reduction. The resulting aryl- and alkyl-substituted branched α-olefins, which are valuable building blocks for synthesis, are obtained in good yields and regioselectivity. A commercially available silane, (TMSO)₂Si(Me)H, is employed as hydride source. This protocol offers a unified alternative to the established metal-catalyzed allylic substitutions with carbon nucleophiles, as no adaption of the catalyst to the nature of the nucleophile is required.