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

Taichi Kusakabe; Tomoyuki Mochida; Tomohiro Ariyama; Dong Lee; Shin Ohkubo; Keisuke Takahashi; Keisuke Kato

doi:10.1039/c9ob01189g

Pd^II catalyzed ligand controlled synthesis of bis(3-furanyl)methanones and methyl 3-furancarboxylates

Org Biomol Chem. 2019 Jul 17;17(28):6860-6865. doi: 10.1039/c9ob01189g.

Authors

Taichi Kusakabe¹, Tomoyuki Mochida², Tomohiro Ariyama¹, Dong Lee¹, Shin Ohkubo¹, Keisuke Takahashi¹, Keisuke Kato¹

Affiliations

¹ Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan. kkk@phar.toho-u.ac.jp.
² Department of Chemistry, Faculty of Sciences, Kobe University, Rokkodai, Nada, Kobe, Hyogo 657-8501, Japan.

PMID: 31268111
DOI: 10.1039/c9ob01189g

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.

Publication types

Research Support, Non-U.S. Gov't