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Synthesis of (Z)-tributylstannyl enynes: systematic studies of Sonogashira cross-coupling reactions between (E)-1-iodovinyl-1-tributylstannanes and terminal acetylenes using amines or tetrabutylammonium hydroxide (TBAOH) as activator |
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| Authors: | Carlos ED NazarioAmanda S Santana Cristiane Y KawasokoCarlos A Carollo Gabriela R HurtadoLuiz H Viana Sandro L BarbosaPalimécio G Guerrero Jr Francisco A MarquesVânia B Dabdoub Miguel J DabdoubAdriano CM Baroni |
| Institution: | a Departamentos de Farmácia-Bioquímica e Química, Universidade Federal do Mato Grosso do Sul, UFMS, Campo Grande/MS, Brazil b Departamento de Farmácia-Bioquímica, Universidade Federal do Vale do Jequitinhonha e Mucuri, Diamantina/MG, Brazil c Departamento de Química e Biologia, DAQBi, Universidade Tecnológica Federal do Paraná, UTFPR, Curitiba/PR, Brazil d Departamento de Química, Universidade Federal do Paraná, UFPR, Curitiba/PR, Brazil e Departamento de Química, Universidade de São Paulo, USP, Campus de Ribeirão Preto/SP, Brazil |
| Abstract: | Sonogashira cross-coupling reactions involving (E)-iodo vinyl stannanes and terminal acetylenes were carried out in the presence of Pd(PPh3)4, CuI and several amines, affording (Z)-tributylstannyl enynes in moderate to good yields (62-91%). Utilizing the catalytic system containing Pd(PPh3)4 (5%), CuI (10%), and TBAOH (40% in aqueous media) as activator, better yields (72-91%) and lower reaction times were achieved. |
| Keywords: | (E)-1-Iodovinyl-1-tributylstannanes (Z)-Tributystannyl enynes Sonogashira cross-coupling reactions Tetrabutylammonium hydroxide (TBAOH) gem-Enediyne |
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