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Issue 28, 2019
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PdII catalyzed ligand controlled synthesis of bis(3-furanyl)methanones and methyl 3-furancarboxylates

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Abstract

The PdII catalyzed carbonylation of allenyl ketones has been investigated. Carbonylative dimerization predominantly proceeded to afford bis(3-furanyl)methanones 2 as the major products. The use of DMSO strikingly changed the course of the reaction, affording methyl 3-furancarboxylates 3 as the major products. DFT calculations revealed that DMSO stabilized the methanol-coordinated intermediate, leading to methoxycarbonylation. Substituted furans 2 and 3 were selectively synthesized from the same allenyl ketone substrate.

Graphical abstract: PdII catalyzed ligand controlled synthesis of bis(3-furanyl)methanones and methyl 3-furancarboxylates

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Article information


Submitted
21 May 2019
Accepted
21 Jun 2019
First published
24 Jun 2019

Org. Biomol. Chem., 2019,17, 6860-6865
Article type
Paper

PdII catalyzed ligand controlled synthesis of bis(3-furanyl)methanones and methyl 3-furancarboxylates

T. Kusakabe, T. Mochida, T. Ariyama, D. Lee, S. Ohkubo, K. Takahashi and K. Kato, Org. Biomol. Chem., 2019, 17, 6860
DOI: 10.1039/C9OB01189G

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