One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzo[b]chalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes

A transition‐metal‐free one‐pot synthesis of 3‐halo‐2‐organochalcogenylbenzo[b]chalcogenophenes 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, s...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-05, Vol.363 (10), p.2610-2618
Main Authors: 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.
Format: Article
Language:English
Subjects:
1-(2,2-dibromovinyl)-2-organochalcogenylbenzenes
benzo[b]chalcogenophenes
chalcogenoacetylenes
one-pot
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Summary:A transition‐metal‐free one‐pot synthesis of 3‐halo‐2‐organochalcogenylbenzo[b]chalcogenophenes 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 benzo[b]chalcogenophenes 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001586