4-Organochalcogenoyl-1H-1,2,3-triazoles: synthesis and functionalization by a nickel-catalyzed Negishi cross-coupling reaction


Autoria(s): Stefani, Helio Alexandre; Leal, Daiana Martins; Manarin, Flávia Giovana
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

29/10/2013

29/10/2013

2012

Resumo

A general method for the synthesis of triazoles containing selenium and tellurium was accomplished via a CuCAAC reaction between organic azides and a terminal triple bond, generated by in situ deprotection of the silyl group. The reaction tolerates alkyl and arylazides, with alkyl and aryl substituents directly bonded to the chalcogen atom. The products were readily functionalized by a nickel-catalyzed Negishi cross-coupling reaction, furnishing the aryl-heteroaryl products at the 4-position in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo [FAPESP07/59404-2, 10/15677-8]

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo

Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)

Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [300.613/2007-5, 152208/2010-0]

Identificador

TETRAHEDRON LETTERS, OXFORD, v. 53, n. 48, supl. 1, Part 1, pp. 6495-6499, 47058, 2012

0040-4039

http://www.producao.usp.br/handle/BDPI/36558

10.1016/j.tetlet.2012.09.062

http://dx.doi.org/10.1016/j.tetlet.2012.09.062

Idioma(s)

eng

Publicador

PERGAMON-ELSEVIER SCIENCE LTD

OXFORD

Relação

TETRAHEDRON LETTERS

Direitos

closedAccess

Copyright PERGAMON-ELSEVIER SCIENCE LTD

Palavras-Chave #SELENIUM #TELLURIUM #TRIAZOLES #NICKEL #NEGISHI #AZIDE-ALKYNE CYCLOADDITION #ORGANOZINC REAGENTS #TERMINAL ALKYNES #CLICK CHEMISTRY #SOLID-PHASE #TELLURIDES #SELENIUM #SALTS #CHEMISTRY, ORGANIC
Tipo

article

original article

publishedVersion