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
| Autor: | Gabriela R. Hurtado, V B Dabdoub, Sandro L. Barbosa, Palimécio G. Guerrero, Miguel J. Dabdoub, Adriano C. M. Baroni, Carlos Alexandre Carollo, Amanda S. Santana, Cristiane Y. Kawasoko, Francisco A. Marques, Carlos Eduardo Domingues Nazario, Luiz Henrique Viana |
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| Rok vydání: | 2011 |
| Předmět: |
(Z)-Tributystannyl enynes
Aqueous medium Chemistry Tetrabutylammonium hydroxide Organic Chemistry gem-Enediyne Sonogashira coupling (E)-1-Iodovinyl-1-tributylstannanes Sonogashira cross-coupling reactions Medicinal chemistry Biochemistry Coupling reaction Catalysis Tetrabutylammonium hydroxide (TBAOH) chemistry.chemical_compound Activator (phosphor) Drug Discovery Organic chemistry QUÍMICA |
| Zdroj: | Repositório Institucional da USP (Biblioteca Digital da Produção Intelectual) Universidade de São Paulo (USP) instacron:USP |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2011.06.004 |
| Popis: | Sonogashira cross-coupling reactions involving ( E )-iodo vinyl stannanes and terminal acetylenes were carried out in the presence of Pd(PPh 3 ) 4 , CuI and several amines, affording ( Z )-tributylstannyl enynes in moderate to good yields (62–91%). Utilizing the catalytic system containing Pd(PPh 3 ) 4 (5%), CuI (10%), and TBAOH (40% in aqueous media) as activator, better yields (72–91%) and lower reaction times were achieved. |
| Databáze: | OpenAIRE |
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