Synthesis of Polysubstituted Furans via Rh(II)-Catalyzed [2 + 3] Annulation of N-Sulfonyl-1,2,3-triazoles with Enaminones

• DOI: 10.1021/acs.orglett.3c02771
• Publication Date: 2023-09-28T12:02:30Z
• Authors: Xiaoqiang Lei; Juan Feng; Qinglan Guo; Yuanhe Li; Jiangong Shi
• Keywords: Annulation; Sulfonyl; Cleavage (geology); Dual role

An unprecedented [2 + 3] annulation of N-sulfonyl-1,2,3-triazoles with enaminones is reported for the access polysubstituted furans. The key to success transformations lies in use Rh(II)-Brønsted acid as cooperative catalysts. Unlike conventional annulations N-sulfony-l-1,2,3-triazoles, Rh(II)-azavinyl carbenes species play dual functions this work, enabled by cleavage C(sp2)-N bond. mechanism studies suggested that an intermolecular rearrangement TsNH- group crucial process.