Premium
One‐Pot Synthesis of 3‐Halo‐2‐organochalcogenylbenzo[ b ]chalcogenophenes from 1‐(2,2‐Dibromovinyl)‐2‐organochalcogenylbenzenes
Author(s) -
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.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001586
Subject(s) - chemistry , chalcogen , halo , acetylide , transition metal , atom (system on chip) , one pot synthesis , stereochemistry , nanotechnology , crystallography , organic chemistry , catalysis , physics , materials science , quantum mechanics , galaxy , computer science , embedded system
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.