Synthesis of 2-(Arylselanyl)benzo[b]chalcogenophenes via 
Intramolecular Cyclization of Vinyl Selenides

Guilherme Stach; Thiago J. Peglow; Juliano A. Roehrs; Filipe Penteado; Thiago Barcellos; Raquel G. Jacob; Eder J. Lenardão; Gelson Perin

doi:10.1055/s-0037-1610656

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(02): 578-586
DOI: 10.1055/s-0037-1610656

paper

Synthesis of 2-(Arylselanyl)benzo[b]chalcogenophenes via Intramolecular Cyclization of Vinyl Selenides

Guilherme Stach

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil eMail: lenardao@ufpel.edu.br eMail: gelson_perin@ufpel.edu.br

,

Thiago J. Peglow

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil eMail: lenardao@ufpel.edu.br eMail: gelson_perin@ufpel.edu.br

,

Juliano A. Roehrs

^bInstituto Federal de Educação Ciência e Tecnologia Sul-rio-grandense – IFSul, 96015-360, Pelotas, RS, Brazil

,

Filipe Penteado

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil eMail: lenardao@ufpel.edu.br eMail: gelson_perin@ufpel.edu.br

,

Thiago Barcellos

^cLaboratório de Biotecnologia de Produtos Naturais e Sintéticos - Universidade de Caxias do Sul – UCS, Caxias do Sul, RS, Brazil

,

Raquel G. Jacob

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil eMail: lenardao@ufpel.edu.br eMail: gelson_perin@ufpel.edu.br

,

Eder J. Lenardão *

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil eMail: lenardao@ufpel.edu.br eMail: gelson_perin@ufpel.edu.br

,

Gelson Perin*

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil eMail: lenardao@ufpel.edu.br eMail: gelson_perin@ufpel.edu.br

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Abstract

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Abstract

An efficient protocol to access 2-arylselanylbenzo[b]chalcogenophene derivatives through the Cu(I)-catalyzed annulation of vinyl selenides is described. The key vinyl selenides were easily prepared from properly functionalized 1,1-dibromostyrenes and the method allowed the synthesis of 2-arylselanylfurans, -thiophenes, and -selenophenes in moderate to excellent yields.

Key words

2-arylselanylbenzo[b]chalcogenophenes - copper catalysis - annulation

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