Published in
Elsevier, Tetrahedron Letters, 32(52), p. 4177-4181, 2011
DOI: 10.1016/j.tetlet.2011.06.004
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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
Journal article published in 2011 by
Carlos E. D. Nazario 
,
Amanda S. Santana,
Cristiane Y. Kawasoko,
Carlos A. Carollo,
Gabriela R. Hurtado,
Luiz H. Viana,
Sandro L. Barbosa,
Palimécio G. Guerrero,
Francisco A. Marques,
Vânia B. Dabdoub,
Miguel J. Dabdoub,
Adriano C. M. Baroni
,
Amanda S. Santana,
Cristiane Y. Kawasoko,
Carlos A. Carollo,
Gabriela R. Hurtado,
Luiz H. Viana,
Sandro L. Barbosa,
Palimécio G. Guerrero,
Francisco A. Marques,
Vânia B. Dabdoub,
Miguel J. Dabdoub,
Adriano C. M. Baroni
This paper is made freely available by the publisher.
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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.