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
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
19/10/2012
19/10/2012
2011
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| Resumo |
Sonogashira cross-coupling reactions involving (E)-iodo vinyl stannanes and terminal acetylenes were carried out in the presence of Pd(PPh(3))(4), Cul and several amines, affording (Z)-tributylstannyl enynes in moderate to good yields (62-91%). Utilizing the catalytic system containing Pd(PPh(3))(4) (5%), Cul (10%), and TBAOH (40% in aqueous media) as activator, better yields (72-91%) and lower reaction times were achieved. (C) 2011 Elsevier Ltd. All rights reserved. FUNDECT-MS PROPP-UFMS CNPq |
| Identificador |
TETRAHEDRON LETTERS, v.52, n.32, p.4177-4181, 2011 0040-4039 http://producao.usp.br/handle/BDPI/20865 10.1016/j.tetlet.2011.06.004 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Tetrahedron Letters |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #(E)-1-Iodovinyl-1-tributylstannanes #(Z)-Tributystannyl enynes #Sonogashira cross-coupling reactions #Tetrabutylammonium hydroxide (TBAOH) #gem-Enediyne #PHASE-TRANSFER CATALYSIS #ENANTIOSELECTIVE SYNTHESIS #SILVER(I) OXIDE #Y-ENYNE #ALKALOIDS #ENEDIYNES #1,1-DIBROMO-1-ALKENES #STANNYLACETYLENES #HYDROZIRCONATION #CHEMISTRY #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
