Issue 40, 2018
From the journal:

Chemical Communications

Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles†

Hirokazu Tsukamoto, ORCID logo *a   Kazuya Itoa  and  Takayuki Doi ORCID logo a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki-aza aoba 6-3, Aoba-ku, Sendai 980-8578, Japan
E-mail: hirokazu@mail.pharm.tohoku.ac.jp
Fax: +81 22 795 6867
Tel: +81 22 795 6867

Abstract

Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.

Graphical abstract: Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

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Article information

DOI
https://doi.org/10.1039/C8CC02589D
Article type
Communication
Submitted
30 Mar 2018
Accepted
20 Apr 2018
First published
23 Apr 2018

Chem. Commun., 2018,54, 5102-5105

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Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

H. Tsukamoto, K. Ito and T. Doi, Chem. Commun., 2018, 54, 5102 DOI: 10.1039/C8CC02589D

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