Stereoselective Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates with alkenyl bromides.
J Org Chem
; 70(10): 3950-6, 2005 May 13.
Article
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| MEDLINE
| ID: mdl-15876083
ABSTRACT
[reaction see text] The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF-H2O (101). A variety of functional groups are tolerated in both coupling partners.
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Banco de datos:
MEDLINE
Asunto principal:
Boratos
/
Bromo
/
Alquenos
Idioma:
En
Año:
2005
Tipo del documento:
Article