Styryl coupling vs. styryl acetate formation in reactions of styryl tellurides with palladium(II) salts
摘要:
In sharp contrast to the expected formation of a telluride-palladium complex, the treatment of either (E,E)- and (Z,Z)-distyryl tellurides (1 and 2) or (E)- and (Z)-styryl phenyl tellurides (5 and 6) with Li2PdCl4 in acetonitrile at 25-degrees-C results in the formation of stereoisomeric 1,4-diphenylbuta-1,3-dienes, whereas the treatment of 1 and 2 with Pd(OAc)2 produces styryl acetates solely or mainly.
Stereoselective Synthesis of Enynes by Nickel-Catalyzed Cross-Coupling of Divinylic Chalcogenides with Alkynes
摘要:
(Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.
Preparation of symmetrical divinyl tellurides via an ylidation reaction
作者:Claudio C Silveira、Gelson Perin、Paula Boeck、Antonio L Braga、Nicola Petragnani
DOI:10.1016/s0022-328x(99)00090-x
日期:1999.7
Symmetrical divinyl tellurides are prepared by sequential reaction of bis-(triphenylmethyl phosphonium) halotellurate with base or by the reaction of triphenylmethylidene phosphoranes with TeCl4, followed by aldehydes. The products are converted to E-α,β-unsaturated aldehydes by treatment with n-BuLi and DMF.
Palladium-catalyzed cross-coupling reactions between organic tellurides and alkenes
作者:Yoshiaki Nishibayashi、Chan Sik Cho、Sakae Uemura
DOI:10.1016/0022-328x(95)05763-f
日期:1996.1
Diaryl tellurides, alkenyl aryl tellurides and dialkenyl tellurides react efficiently with various alkenes in methanol in the presence of a catalytic amount of PdCl2 together with AgOAc and Et(3)N to give the corresponding aryl- and alkenyl-substituted alkenes with moderate to quantitative yields. Both monomeric and dimeric palladium complexes, (Ph(2)Te)(2)PdCl2 and [(Ph(2)Te)PdCl2](2) respectively, react readily with alkenes to give a high yield of phenyl-substituted alkenes. The key step of this coupling reaction is proposed to be the migration of an organic moiety from Te to Pd (transmetallation) in organic telluride-PdCl2 complexes to afford organopalladium species.
Palladium-catalyzed homocoupling reactions of organic tellurides
作者:Yoshiaki Nishibayashi、Chan Sik Cho、Kouichi Ohe、Sakae Uemura
DOI:10.1016/s0022-328x(96)06561-8
日期:1996.12
Organic tellurides containing a styryl moiety react in acetonitrile to give the corresponding homocoupling products, 1,3-dienes, with moderate to quantitative yields in the presence of a catalytic amount of Pd(OAc)(2) together with AgOAc at 25 degrees C. In contrast, such homocoupling reactions hardly occur with diaryl, alkyl aryl, dialkyl, and alkynyl aryl tellurides, even at reflux temperature and in the presence of a stoichiometric amount of palladium salt, in disagreement with reported results. The result of cross-over experiments suggests that this homocoupling reaction occurs between an alkenyl telluride and an alkenylpalladium species, the latter being formed via the migration of an alkenyl moiety from Te to Pd (transmetallation).
BARROS, SIMONE M.;DABDOUB, MIGUEL J.;DABDOUB, VANIA M. B.;COMASSETO, JOAO+, ORGANOMETALLICS, 8,(1989) N, C. 1661-1665
作者:BARROS, SIMONE M.、DABDOUB, MIGUEL J.、DABDOUB, VANIA M. B.、COMASSETO, JOAO+