- A procedure for the oxidative 'dimerization' of aliphatic 1-alkynes
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Aliphatic 1-alkynes RC≡CH (R = alkyl) are readily converted into diynes RC≡CC≡CR, by introducing oxygen into a mixture of the acetylene and pyridine using copper(I)bromide as a catalyst and 1,8-diazabicyclo[5.4.0] undec-7-ene as a co-catalyst.
- Brandsma,Verkruijsse,Walda
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- Palladium-catalyzed acylation and/or homo-coupling of aryl- and alkyl-acetylenes
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Allyl or benzyl halides, through a Pd(0)-catalyzed reaction and under CO pressure, generate acyl-palladium/halides that, in the presence of a base and an aryl- and alkyl-acetylene, undergo nucleophilic acyl substitution giving conjugated acetylenic ketones. Diynes, resulting from alkyne/alkyne homo-coupling, were instead the main products in reactions performed without allyl or benzyl halides. Moreover, dimerization, trimerization, and cyclotrimerization reactions of acetylenes were observed in reaction carried out even without base.
- Perrone, Serena,Bona, Fabio,Troisi, Luigino
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experimental part
p. 7386 - 7391
(2011/10/09)
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- UTILIZATION OF "BIS(TRIPHENYLPHOSPHINE)PALLADIUM" AS CATALYST IN THE CROSS COUPLING REACTION OF TERMINAL ACETYLENES WITH ALKENYL HALIDES
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Utilization of the 14-electron species "bis(triphenylphosphine)palladium (0)" as catalyst has been extended to the cross coupling reaction of a terminal acetylene with an alkenyl halide to prepare conjugated enynes, such as (Z)-11-hexadecen-13-ynyl acetate 1, which are direct precursors of Z,Z and Z,E dienyc unsaturated systems.
- Champs, F.,Chamorro, E.,Gasol, V.,Guerrero, A.
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p. 3211 - 3220
(2007/10/02)
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- SYNTHESIS OF 4-ALKYL-TRIMETHYLSILYLBUTA-1,3-DIYNES
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Lithium trimethylsilylbutadiyn (2) is alkylated by primary alkyl halides in THF-HMPA or via the ethylenediamine complex (4) in THF-DMSO to give the title compounds (3) in good yield.
- Holmes, Andrew B.,Jones, Graham E.
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p. 3111 - 3112
(2007/10/02)
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