Synthesis of 3-iodothiophenes via iodocyclization of (Z)-thiobutenynes |
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| Authors: | Amanda S. Santana,Diego B. Carvalho,Nadla S. Cassemiro,Luiz H. Viana,Gabriela R. Hurtado,Marcos S. Amaral,Najla M. Kassab,Palimé cio G. Guerrero Jr.,Sandro L. Barbosa,Miguel J. Dabdoub,Adriano C.M. Baroni |
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| Affiliation: | 1. LASQUIM—Laboratório de Síntese e Química Medicinal, Centro de Ciências Biológicas e da Saúde e Instituto de Química, Universidade Federal do Mato Grosso do Sul, UFMS, Campo Grande, MS 79070-900, Brazil;2. Departamento de Química e Biologia, DAQBi, Universidade Tecnológica Federal do Paraná, UTFPR, Curitiba, PR 80230-901, Brazil;3. Departamento de Farmácia-Bioquímica, Universidade Federal do Vale do Jequitinhonha e Mucuri, Diamantina, MG 39100-000, Brazil;4. Departamento de Química, Universidade de São Paulo, Av. Bandeirantes, 3900, Ribeirão Preto, SP 14040-901, Brazil |
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| Abstract: | ![]()
A simple synthesis of 3-iodothiophenes was demonstrated using a wide range of (Z)-thioenynes. The key step in the iodocyclofunctionalization was the selective reduction of the triple bond in (Z)-thioenynes by the addition of iodine as an electrophilic agent. The 3-iodothiophenes were obtained in good to excellent yields of 61–92%. The 3-iodothiophenes were used as substrates in Sonogashira cross-coupling reactions to obtain thiophene acetylenes. |
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| Keywords: | ( boldFont" >Z)-Thiobutenynes Iodocyclization 3-Iodothiophenes Sonogashira cross coupling |
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