Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans

Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans

Author Rossini, Allan Felipe da Costa Autor UNIFESP Google Scholar
Frota, Carlise Google Scholar
Casagrande, Gleison Antonio Google Scholar
Pizzuti, Lucas Google Scholar
Raminelli, Cristiano Autor UNIFESP Google Scholar
Institution Universidade Federal de São Paulo (UNIFESP)
Universidade Federal da Grande Dourados Faculdade de Ciências Exatas e Tecnologia
Abstract The coupling reaction between 2,6-diiodoanisoles and terminal alkynes using Pd(PPh3)2Cl2 and CuI as catalysts and diisopropylamine as base in toluene at room temperature for 12 h produced selectively alkynylated 2-iodoanisoles, in good to excellent yields (52-95%), which are useful building blocks with potential application in the synthesis of functionalized benzo[b]furans.

A reação de acoplamento entre 2,6-diiodoanisóis e alcinos terminais usando Pd(PPh3)2Cl2 e CuI como catalisadores e diisopropilamina como base em tolueno a temperatura ambiente por 12 h produziu seletivamente 2-iodoanisóis aquinilados, em rendimentos de bons a excelentes (52-95%), os quais são blocos de construção úteis com potencial aplicação na síntese de benzo[b]furanos funcionalizados.
Keywords Sonogashira reaction
selective mono-coupling
alkynylated anisoles
diiodinated benzo[b]furans
palladium and copper catalysis
Language English
Sponsor Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Fundacao de Apoio ao Desenvolvimento do Ensino
Ciencia e Tecnologia do Estado de Mato Grosso do Sul (FUNDECT)
Date 2014-11-01
Published in Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 11, p. 2125-2132, 2014.
ISSN 0103-5053 (Sherpa/Romeo, impact factor)
1678-4790 (Sherpa/Romeo, impact factor)
Publisher Sociedade Brasileira de Química
Extent 2125-2132
Origin http://dx.doi.org/10.5935/0103-5053.20140200
Access rights Open access Open Access
Type Article
Web of Science ID WOS:000345241700026
SciELO ID S0103-50532014001100026 (statistics in SciELO)
URI http://repositorio.unifesp.br/handle/11600/8653

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