Enantioselective Intermolecular C–H Functionalization of Allylic and Benzylic sp3 C–H Bonds Using N-Sulfonyl-1,2,3-triazoles

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• 作者：Robert W. Kubiak II ; Jeffrey D. Mighion ; Sidney M. Wilkerson-Hill ; Joshua S. Alford ; Tetsushi Yoshidomi ; Huw M. L. Davies
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3118-3121
• 全文大小：384K
• 年卷期：0
• ISSN：1523-7052

文摘

The enantioselective intermolecular sp³ C–H functionalization at the allylic and benzylic positions was achieved using rhodium-catalyzed reactions with 4-phenyl-N-(methanesulfonyl)-1,2,3-triazole. The optimum dirhodium tetracarboxylate catalyst for these reactions was Rh₂(S-NTTL)₄. The rhodium-bound α-imino carbene intermediates preferentially reacted with tertiary over primary C–H bonds in good yields and moderate levels of enantioselectivity (66–82% ee). This work demonstrates that N-sulfonyltriazoles can be applied to the effective C–H functionalization at sp³ C–H bonds of substrates containing additional functionality.