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Synthesis of 2‐Organylchalcogenyl–benzo[ b ]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization
Author(s) -
Perin Gelson,
Roehrs Juliano A.,
Hellwig Paola S.,
Stach Guilherme,
Barcellos Thiago,
Lenardão Eder J.,
Jacob Raquel G.,
Luz Eduardo Q.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700948
Subject(s) - sonogashira coupling , chemistry , electrophile , suzuki reaction , combinatorial chemistry , stereochemistry , organic chemistry , palladium , catalysis
A convenient synthesis of 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes was established taking advantage of the selective reaction of 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes with thiols or diorganyl diselenides. The new 1‐(2‐chalcogenylethynyl)‐2‐butylselenanylbenzenes were prepared in good yields and used as precursors of 2‐organylchalcogenylbenzo[ b ]selenophenes via electrophilic cyclization using I 2 , Br 2 or PhSeBr as electrophiles. Different classes of new 3‐substituted‐ (3‐iodo, 3‐bromo, 3‐phenylselenanyl) benzo[ b ]selenophenes were prepared in good yields. The synthetic application of the obtained products was demonstrated employing the benzo[ b ]selenophenes in Suzuki and Sonogashira cross‐coupling reactions.