Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides
Copper(II) acetate catalysed ring-opening cross-coupling of cyclopropanols with sulfonyl azides
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DOI：
10.1039/c5ra20729k
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发表时间：
2015-11
期刊：
影响因子：
3.9
通讯作者：
Mei-Hua Shen;Xiaodong Lu;Hua-Dong Xu
中科院分区：
文献类型：
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作者：
Mei-Hua Shen;Xiaodong Lu;Hua-Dong Xu
开发了乙酸铜(II)催化的环丙醇与磺酰叠氮化物的开环交叉偶联。通过这种方法，可以以中等到高产率有效地制备各种β-氨基酮，并且古老的官能团（例如苄基C-H、烷基和芳基溴、烷基磺酸酯、甲硅烷基醚和烯烃）与这些反应条件兼容。对照实验排除了自由基和简单铜氮宾中间体的参与，并提出了一种可能的机制，其特征在于开环金属化和烷基迁移插入铜氮宾的关键步骤。
A copper(II) acetate catalyzed ring-opening cross-coupling of cyclopropanol with sulfonyl azide has been developed. By this method, various β-amino ketones have been made efficiently in medium to high yields and venerable functional groups such as benzylic C–H, alkyl and aryl bromides, alkyl sulfonate, silyl ether and alkene are compatible with these reaction conditions. Control experiments have precluded the involvement of both radical and simple copper nitrene intermediates and a possible mechanism featuring key steps of ring-opening metalation and alkyl group migratory insertion into copper nitrene has been proposed.