C(sp2)-H selenylation of substituted benzo[4,5]imidazo[2,1- b]thiazoles using phenyliodine(iii)bis(trifluoroacetate) as a mediator

Prasanjit Ghosh; Gautam Chhetri; Anirban Mandal; Yu Chen; William H Hersh; Sajal Das

doi:10.1039/d4ra00057a

C(sp²)-H selenylation of substituted benzo[4,5]imidazo[2,1- b]thiazoles using phenyliodine(iii)bis(trifluoroacetate) as a mediator

RSC Adv. 2024 Feb 2;14(7):4462-4470. doi: 10.1039/d4ra00057a. eCollection 2024 Jan 31.

Authors

Prasanjit Ghosh¹, Gautam Chhetri¹, Anirban Mandal¹, Yu Chen^{2

3}, William H Hersh^{2

3}, Sajal Das¹

Affiliations

¹ Department of Chemistry, University of North Bengal Darjeeling-734013 India prasanjitmeister@yahoo.com sajal.das@hotmail.com sajaldas@nbu.ac.in.
² Department of Chemistry and Biochemistry, Queens College and the Graduate Centre of City University of New York Flushing New York 11367-1597 USA yu.chen1@qc.cuny.edu.
³ PhD Program in Chemistry, The Graduate Center of the City University of New York 365 Fifth Ave. New York 10016 USA.

Abstract

Herein, an expeditious metal-free regioselective C-H selenylation of substituted benzo[4,5]imidazo[2,1-b]thiazole derivatives was devised to synthesize structurally orchestrated selenoethers with good to excellent yields. This PIFA [bis(trifluoroacetoxy)iodobenzene]-mediated protocol operates under mild conditions and offers broad functional group tolerance. In-depth mechanistic investigation supports the involvement of radical pathways. Furthermore, the synthetic utility of this methodology is portrayed through gram-scale synthesis.