Cyclization-carbonylation of α,β-alkynic hydrazones and (o-alkynylphenyl) (methoxymethyl) sulfides with Pd(tfa)2 in DMSO/MeOH afforded methyl pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates, respectively, in good yields. A simple change of the ligand (solvent) allowed controlled, effective switching between cyclization-carbonylation-cyclization-coupling (CCC-coupling) reactions and cyclization-carbonylation reactions.
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Pd(II)-catalyzed ligand controlled synthesis of pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates.
Org Biomol Chem
November 2014
Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
Cyclization-carbonylation of α,β-alkynic hydrazones and (o-alkynylphenyl) (methoxymethyl) sulfides with Pd(tfa)2 in DMSO/MeOH afforded methyl pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates, respectively, in good yields. A simple change of the ligand (solvent) allowed controlled, effective switching between cyclization-carbonylation-cyclization-coupling (CCC-coupling) reactions and cyclization-carbonylation reactions.
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