Lei Xiaoqiang, Feng Juan, Guo Qinglan, Li Yuanhe, Shi Jiangong
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
School of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, China.
Org Lett. 2023 Oct 13;25(40):7338-7343. doi: 10.1021/acs.orglett.3c02771. Epub 2023 Sep 28.
An unprecedented [2 + 3] annulation of -sulfonyl-1,2,3-triazoles with enaminones is reported for the access of polysubstituted furans. The key to the success of the transformations lies in the use of Rh(II)-Brønsted acid as cooperative catalysts. Unlike the conventional annulations of -sulfony-l-1,2,3-triazoles, the Rh(II)-azavinyl carbenes species play dual functions in this work, enabled by the cleavage of the C(sp)N bond. The mechanism studies suggested that an intermolecular rearrangement of the TsNH group is crucial to the annulation process.
据报道，通过前所未有的磺酰基-1,2,3-三唑与烯胺酮的[2 + 3]环化反应可合成多取代呋喃。该转化反应成功的关键在于使用铑（II）-布朗斯特酸作为协同催化剂。与传统的磺酰基-1,2,3-三唑环化反应不同，铑（II）-氮杂乙烯基卡宾物种在这项工作中发挥了双重作用，这是由C(sp)N键的断裂所促成的。机理研究表明，对甲苯磺酰胺基（TsNH）的分子间重排对环化过程至关重要。
