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铜催化的烯丙基和苄基碳氢键的酰胺化反应。

Copper-catalyzed amidation of allylic and benzylic C-H bonds.

作者信息

Pelletier Guillaume, Powell David A

机构信息

Merck Frosst Centre for Therapeutic Research, 16711 Trans Canada Highway, Kirkland, Québec H9H 3L1, Canada.

出版信息

Org Lett. 2006 Dec 21;8(26):6031-4. doi: 10.1021/ol062514u.

Abstract

[Structure: see text] A copper-catalyzed amidation of allylic and benzylic C-H bonds with both primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a diverse set of hydrocarbon species with aryl, heteroaryl, and alkyl sulfonamides and is tolerant of a variety of functional groups. Mechanistic insight has been gained through the isolation of a benzylic acetate intermediate, which was demonstrated to undergo facile conversion to the substituted sulfonamide product under copper catalysis.

摘要

[结构:见正文] 本文描述了一种铜催化的烯丙基和苄基C-H键与伯磺酰胺和仲磺酰胺的酰胺化反应。该反应适用于多种烃类与芳基、杂芳基和烷基磺酰胺的偶联,并且耐受多种官能团。通过分离出苄基乙酸酯中间体获得了机理上的认识,该中间体在铜催化下可轻松转化为取代磺酰胺产物。

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