Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
College of Chemistry and Chemical Engineering, Yangzhou University , 180 Siwangting Road, Yangzhou 225002, China.
Org Lett. 2017 Mar 17;19(6):1434-1437. doi: 10.1021/acs.orglett.7b00373. Epub 2017 Mar 6.
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.
发展了一种通用的 Pd 催化 N-甲磺酰酰胺与芳基硼酸的 Suzuki-Miyaura 交叉偶联反应，通过选择性的 N-C 断裂。所呈现的结果代表了首例通过原子经济性、廉价和良性的甲磺酰基来激活酰胺的过渡金属催化交叉偶联反应。该反应通过酰胺 N-C 键的化学选择性断裂，以高效率提供具有多种有用官能团的芳基化产物。讨论了反应的范围和高选择性的来源。还提出了 N-甲磺酰基取代基对无环酰胺中键活化的有益影响。
