One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzochalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

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One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzochalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

Luz, Eduardo Q; Silvério, Gabriel L; Seckler, Diego; Lima, David B; Santana, Francielli S; Barbosa, Ronilson V; Montes D'Oca, Caroline R; Rampon, Daniel S

Advanced synthesis & catalysis, 05/2021, Volume: 363, Issue: 10

Journal Article

A transition‐metal‐free one‐pot synthesis of 3‐halo‐2‐organochalcogenylbenzobchalcogenophenes has been developed using 1‐(2‐organochalcogenylethynyl)‐2‐butylchalcogenylbenzenes generated in situ from 1‐(2,2‐dibromovinyl)‐2‐organochalcogenylbenzenes and diorganoyl dichalcogenides. By this method, several 2,3‐disubstituted benzobchalcogenophenes were prepared in yields of 48–93%. The mechanistic investigation suggests that the formation of chalcogenoacetylenes containing an adjacent chalcogen atom in the first step of this one‐pot procedure involves acetylide anions formed from 1‐(2,2‐dibromovinyl)‐2‐organochalcogenylbenzenes and mild bases.

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