Synthesis and structural features of a series of Cu(i) furan-2-thiocarboxylate complexes: efficient “click” catalysts for the synthesis of glycoconjugates and glycocluster

Abstract

Cu(I) furan-2-thiocarboxylate complexes [(PPh3)2Cu(fCOS)2] (1), [(PPh3)2Cu(fCOS)2.H2O] (2), [(dppf)Cu(fCOS).CH3CN] (3), [(PPh3)3Cu(µ-fCOS)(µ-Cl)] (4), and [(dppee)Cu(µ-fCOS)]2 (5) (where dppee = 1,1՛-bis(diphenylphosphinoethene), dppf = 1,1՛-bis(diphenylphosphinoferrocene), fCOS¯ = furan-2-thiocarboxylate ion) have been synthesized. The complexes...

Synthesis of a series of Cd(ii) furan-2-thiocarobxylates: unprecedented coordination geometry of a Cd(ii) complex exhibiting catalytic efficiency for the synthesis of 3,4-dihydropyrimidine-2(1H)-one derivatives

“…Synthesis of the ligand acid, fCOSH was accomplished by following a reported procedure. 44,45 Synthesis of [(PPh 3 ) 2 Cd(SCOf) 2 ] (1)…”

Synthesis and structural features of indium(iii) furan-2-thiocarboxylates showing efficient catalytic activity toward multicomponent reactions via Knoevenagel condensation

“…A methanolic solution (10 mL) of furan-2-thiocarboxylic acid 39 (0.128 g, 1 mmol) was added dropwise to a methanolic solution (5 mL) of triethylamine (139 μL, 1 mmol) in a 50 mL round-bottomed flask kept in an ice bath. After 15 min, indium trichloride (0.054 g, 0.25 mmol) in methanol (5 mL) was added to the above flask.…”

Growing Impact of Intramolecular Click Chemistry in Organic Synthesis

“…Although CuI/DIPEA (Medal's catalytic system) [2] and CuSO 4 .5H 2 O/NaAsc (Sharpless Catalytic system) [3] both were most routinely utilized in regioselective 1,4-disubstituted triazole formation reactions, but not limited as a number of other catalytic systems were also explored in azide-alkyne reactions. [67][68][69][70][71][72][73] For example, Sen and co-workers developed a straightforward method for the high-yielding synthesis of 1,4,5-trisubstituted triazole via Sonogashira coupling reaction followed by intramolecular click coupling. [74] The methods believe to precede the Sonogashira coupling of terminal alkyne of glycosyl azido-alkyne 16 with aryl iodide in the presence of cuprous oxide-nanoparticle under basic condition (Cs 2 CO 3 was used as a base) in aqueous media and resulted to aryl substituted azido-alkyne sugar which on subsequent intramolecular click conjugation afforded the desired fused glycohybrid triazole 17 in 85 % yield (Scheme 3).…”

“…Although CuI/DIPEA (Medal's catalytic system) [2] and CuSO 4 .5H 2 O/NaAsc (Sharpless Catalytic system) [3] both were most routinely utilized in regioselective 1,4‐disubstituted triazole formation reactions, but not limited as a number of other catalytic systems were also explored in azide‐alkyne reactions [67–73] . For example, Sen and co‐workers developed a straightforward method for the high‐yielding synthesis of 1,4,5‐trisubstituted triazole via Sonogashira coupling reaction followed by intramolecular click coupling [74] .…”