86148-27-8Relevant academic research and scientific papers
Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling.
Savarin,Srogl,Liebeskind
, p. 91 - 93 (2007/10/03)
[figure: see text] A new methodology for the synthesis of substituted alkynes is described. In the presence of copper(I) thiophene-2-carboxylate (CuTC) or copper (I) 3-methylsalicylate (CuMeSal), the palladium-catalyzed cross-coupling of thioalkyne derivatives with boronic acids affords functionalized alkynes in yields ranging from 39 to 91%. This coupling occurs efficiently under mild, nonbasic conditions with a wide variety of thioalkynes and boronic acids, providing a reaction complementary to the Sonogashira protocol.
Phase transfer catalysis in synthesis of organylthio(organyltelluro) acetylenes
Martynov, Alexander V.,Mirskova, Anna N.,Le Guillanton, Georges
, p. 245 - 250 (2007/10/03)
Phase transfer reaction of diorganyl ditellurides with organyl-2,2-dichlorovinyl sulfides, using as phase transfer catalysts benzyltriethylammonium chloride or 18-crown-6 ether, was used as a new general method to prepare organylthio(organyltelluro)acetylenes R-S-C≡C-Te-R′. The organyltellurolate anion formed in the presence of NaOH is the reaction intermediate.
A New Approach to the Synthesis of Symmetrical Bis(organylchalcogeno)acetylenes: Scope and Limitations
Martynov, Alexander V.,Guillanton, Georges Le
, p. 823 - 831 (2007/10/03)
A new general method to prepare bis(organylchalcogeno)acetylenes R-Y-CC-Y-R (Y = S, Se, Te) by dehydrochlorination of the corresponding 1,2-bis(organylchalcogeno)chloroethylenes R-Y-CH=CCl-Y-R with tert-BuOK/tert-BuOH and/or KOH/DMSO is developed.Dechlorination of 1,2-bis(organylchalcogeno)-1,2-dichloroethylenes R-Y-CCl=CCl-Y-R (Y = S, Se, Te) with BuLi in ether or THF is effective only for sulfur derivatives.With Y = Se and alkyl substituents, substitution of the chlorine atom by a butyl group takes place giving rise to 5,6-bis(alkylseleno)dec-5-ene .With aryl substituents, an attack of the ArSe-group by the Bu-radical is observed leading to an aryl butyl selenide.In the case of the tellurium compound Ph-Te-CCl=CCl-Te-Ph, there is a competition between dechlorination to give Ph-Te-CC-Te-Ph, and substitution to produce the phenyl butyl telluride. - Keywords: bis(organylchalcogeno)acetylene; 1,2-bis(organylchalcogeno)chloroethylene; 1,2-bis(organochalcogeno)-1,2-dichloroethylene.
NUCLEOPHILIC REACTIONS AT A VINYLIC CENTER. XXVIII. FLUOROCHLOROETHENES AND FLUOROBROMOETHENES IN REACTIONS WITH SODIUM ALCOHOLATES AND ARENETHIOLATES
Shainyan, B. A.,Vereshchagin, A. L.
, p. 1981 - 1988 (2007/10/02)
During the reaction of halogenoethenes (Z+E)-CHX=CFX with sodium methoxide and with sodium p-thiocresolate in methanol initial attack by the nucleophilic takes place at the carbon atom attached to the fluorine atom.In the reactions with sodium methoxide the intermediate monosubstitution products are more reactive than the initial halogenoethenes, and the main reaction products are the ortho esters CHXYC(OMe)3.An "element effect", i.e., concurrent substitution of F and Cl(Br) in the reaction with sodium methoxide, was discovered.With sodium p-thiocresolate trifluorochloroethene gives the product from substitution of the chlorine atom and a small amount of the addition product as impurity.The other ethenes give substitution, addition, and halogenophilic reduction products and also the products from further transformations (hydrolysis and decarboxylation).
A broad scope highly efficient synthesis of bis(R-thio)acetylenes
Riera, Antoni,Cabre, Francesc,Moyano, Albert,Pericas, Miquel A.,Santamaria, Jaume
, p. 2169 - 2172 (2007/10/02)
Treatment of dichloroacetylene with two equivalents of a thiol and two equivalents of potassium hydride in THF solution affords the corresponding bis(R-thio)acetylene in high yield.
