A mild method for the regioselective synthesis of propargyl ethers by the coupling of propargyl alcohols with a range of other alcohols is described. The method employs an air- and moisture-tolerant rhenium-oxo complex ((dppm)ReOCl3) as a catalyst for the formation of sp3-carbon-oxygen bonds without the need for prior activation of the propargyl alcohol or deprotonation of the alcohol nucleophi...

The regioselectivity of the model compound 4-methyl-1-thioxo1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one (3) towards different electrophiles was studied. Compound 3 reacts with alkyl and aryl halides to give the corresponding S-substituted derivatives. The reaction of the model thioamide with acyl halides proceeds by the formation of kinetically controlled S-acyl derivatives followe...

[Chemical reaction: See text] The synthesis and unique reactivity of a series of arylsulfonate-based nucleophile assisting leaving groups (NALG) containing oligomeric ether units (including crown ethers) attached to the arylsulfonyl ring in the ortho orientation are described. The reactions of a variety of these ether-containing alkyl sulfonates with metal halides proceeded at substantially gre...

Among cross-coupling reactions, the Suzuki-Miyaura transformation stands out because of its practical advantages, including the commercial availability and low toxicity of the required reagents, mild reaction conditions, and functional group compatibility. Nevertheless, few conditions can be used to cross-couple alkyl boronic acids or esters with aryl halides, especially 2-pyridyl halides. Here...

A novel series of 1,3,4-thiadiazoles, 5-arylazothiazoles and hexahydropyrimido-[4,5-d][1,2,4]triazolo[4,3-a]pyrimidines were synthesized via reaction of hydrazonoyl halides with each of alkyl carbothioates, carbothioamides and 7-thioxo-5,6,7,8-tetrahydropyrimido-[4,5-d]pyrimidine-2,4(1H,3H)-diones in the presence of triethylamine. The structures of the newly synthesized compounds were establish...

A facile reaction of 1-ethyl-3-methylimidazolium acetate ([EMIm]Ac) with dichloromethane at room temperature was observed with esters among the products. This esterification can be exploited for mild solvent-free esterification with a range of other carboxylate-based ionic liquids and alkyl halides.