Cascade Copper-Catalyzed 1,2,3-Trifunctionalization of Terminal Allenes

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• 作者：Wanxiang Zhao ; John Montgomery
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：August 10, 2016
• 年：2016
• 卷：138
• 期：31
• 页码：9763-9766
• 全文大小：359K
• 年卷期：0
• ISSN：1520-5126

文摘

A cascade cyanation/diborylation of terminal allenes proceeds efficiently with copper catalysis using bis(pinacolato)diboron (B₂Pin₂) and N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as reagents. Mechanistic studies suggest that the process proceeds through cyanoborylation of the substituted π-system of the allene followed by hydroboration of the remaining π-component. A wide array of product derivatives may be accessed through site-selective cross-couplings and N-bromosuccinimide-promoted heteroarylations as well as standard oxidative and reductive conversions of the initially obtained adducts.