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Issue 43, 2014
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Pd(II)-catalyzed ligand controlled synthesis of pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates

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Abstract

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.

Graphical abstract: Pd(ii)-catalyzed ligand controlled synthesis of pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates

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Publication details

The article was received on 25 Jul 2014, accepted on 26 Aug 2014 and first published on 26 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01576B
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 8619-8626
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    Pd(II)-catalyzed ligand controlled synthesis of pyrazole-4-carboxylates and benzo[b]thiophene-3-carboxylates

    Y. D. Dhage, H. Daimon, C. Peng, T. Kusakabe, K. Takahashi, Y. Kanno, Y. Inouye and K. Kato, Org. Biomol. Chem., 2014, 12, 8619
    DOI: 10.1039/C4OB01576B

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