Metal‐Free Oxidative Decarboxylative Heteroannulation of Alkynyl Carboxylic Acids with Sulfinates and tert‐Butyl Nitrite toward 2, 2‐Disulfonyl‐2H‐Azirines. Issue 10 (1st April 2020)

• Record Type: Journal Article
• Authors: Yue, Xin; He, Xingyi; Wu, Yan‐Chen; Hu, Ming; Wu, Shuang; Xie, Ye‐Xiang; Li, Jin‐Heng
• Is Part Of: ChemCatChem. Volume 12:Issue 10(2020)
• Page Start: 2690
• Page End: 2694
• Publication Date: 2020-04-01
• Subjects: annulation -- alkynyl carboxylic acids -- sulfonates -- N-heterocycles -- tert-butyl nitrite; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201902400
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A new TBAF ( tetra butylammonium fluoride)‐promoted TBHP ( tert ‐butyl hydroperoxide)‐mediated decarboxylative heteroannulation cascades of alkynyl carboxylic acids with sodium sulfinates and TBN ( tert ‐butyl nitrite) has been developed for producing 2, 2‐disulfonyl‐2 H ‐azirines under metal‐free conditions. By employing readily available tert ‐butyl nitrite as the nitrogen source, the method enable the formation of four new chemical bonds in a single reaction through decarboxylation, sulfonylatyion and nitrogen‐incorporation annulation cascades, and provides an efficient access to disulfonylated 2 H ‐azirines. Abstract : My nitrogen hat has three corners : A newly developed t ‐BuONO as a nitrogen source and oxidant, metal‐free oxidative decarboxylative heteroannulation of alkynyl carboxylic acids with sulfinates and tert ‐butyl nitrite has been realized, producing the corresponding 2, 2‐Disulfonyl‐2 H ‐Azirines in 53–83 % yields.