Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group
Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group
复制标题
钯催化的 N-甲磺酰胺通过 N-C 断裂的 Suzuki-Miyaura 交叉偶联：甲磺酰基的电子效应
DOI：
10.1021/acs.orglett.7b00373
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发表时间：
2017-03-17
期刊：
影响因子：
5.2
通讯作者：
Szostak, Michal
中科院分区：
文献类型：
--
作者：
Liu, Chengwei;Liu, Yongmei;Szostak, Michal
一种通过选择性N - C键断裂实现的N - 甲磺酰基酰胺与芳基硼酸的钯催化的通用铃木-宫浦交叉偶联反应已经被开发出来。所呈现的结果代表了由一种原子经济、廉价且良性的甲磺酰基活化的酰胺经过渡金属催化交叉偶联的首个实例。该反应通过酰胺N - C键的高效化学选择性断裂，提供了具有一系列有用官能团的芳基化产物。对反应范围和高选择性的来源都进行了讨论。还阐述了N - 甲磺酰基取代基对无环酰胺中键活化的有益影响。
A general Pd-catalyzed Suzuki-Miyaura cross-coupling of N-mesylamides with arylboronic acids by selective N-C cleavage has been developed. The presented results represent the first example of a transition-metal-catalyzed cross-coupling of amides activated by an atom-economic, cheap, and benign mesyl group. The reaction delivers arylated products featuring a range of useful functional groups by chemoselective cleavage of the amide N-C bond with high efficiency. Both the scope and the origin of high selectivity are discussed. A beneficial effect of the N-mesyl substituent on the bond activation in acyclic amides is presented.