Regioselective C–H sulfenylation of N-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles. Issue 53 (27th August 2020)

• Record Type: Journal Article
• Authors: Hu, Jingyan; Ji, Xiaoming; Hao, Shuai; Zhao, Mingqin; Lai, Miao; Ren, Tianbao; Xi, Gaolei; Wang, Erbin; Wang, Juanjuan; Wu, Zhiyong
• Is Part Of: RSC advances. Volume 10:Issue 53(2020)
• Page Start: 31819
• Page End: 31823
• Publication Date: 2020-08-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0ra06635d
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A novel, practical and highly regioselective TBAI promoted C-3 sulfenylation reaction of N -sulfonyl protected 7-azaindoles with sulfonyl chlorides is presented here. Abstract : This paper describes the regioselective C-3 sulfenylation of N -sulfonyl protected 7-azaindoles with sulfonyl chlorides. In this transformation, dual roles of TBAI serving as both promoter and desulfonylation reagent have been demonstrated. The reaction proceeded smoothly under simple conditions to afford 3-thio-7-azaindoles in moderate to good yields with broad substrate scopes. This protocol refrains from using transition-metal catalysts, strong oxidants or bases, and shows its practical synthetic value in organic synthesis.