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

• Published in: Tetrahedron letters Vol. 52; no. 32; pp. 4177 - 4181
• Main Authors: Nazario, Carlos E.D., Santana, Amanda S., Kawasoko, Cristiane Y., Carollo, Carlos A., Hurtado, Gabriela R., Viana, Luiz H., Barbosa, Sandro L., Guerrero, Palimécio G., Marques, Francisco A., Dabdoub, Vânia B., Dabdoub, Miguel J., Baroni, Adriano C.M.
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 10-08-2011; Elsevier
• Subjects: (E)-1-Iodovinyl-1-tributylstannanes; (Z)-Tributystannyl enynes; Aliphatic compounds; Amines; Catalysis; Chemical reactions; Chemistry; Exact sciences and technology; gem-Enediyne; Hydroxides; Organic chemistry; Preparations and properties; Reaction time; Sonogashira cross-coupling reactions; Synthesis (chemistry); Terminals; Tetrabutylammonium hydroxide (TBAOH); Tetrahedrons; Sonogashira cross-coupling reactions; Tetrabutylammonium hydroxide (TBAOH); (E)-1-Iodovinyl-1-tributylstannanes; (Z)-Tributystannyl enynes; gem-Enediyne; Catalytic reaction; Acetylenic compound; Palladium complex; Tetrabutylammonium hydroxide (TBAOH) gem-Enediyne; Iodine Organic compounds; Enynic compound; Organic iodine compounds; (E)-1-lodovinyl-1-tributylstannanes; Amine; Vinylic compound; Copper I Iodides; Aqueous solution; Chemical synthesis; Organic stannane
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.06.004

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.