Synthesis of substituted tetrahydrocyclobuta[b]benzofurans by palladium-catalyzed substitution/[2+2] cycloaddition of propargylic carbonates with 2-vinylphenols

Masahiro Yoshida; Shoko Ohno; Kosuke Namba

doi:10.1002/anie.201306903

Synthesis of substituted tetrahydrocyclobuta[b]benzofurans by palladium-catalyzed substitution/[2+2] cycloaddition of propargylic carbonates with 2-vinylphenols

Angew Chem Int Ed Engl. 2013 Dec 16;52(51):13597-600. doi: 10.1002/anie.201306903. Epub 2013 Oct 31.

Authors

Masahiro Yoshida¹, Shoko Ohno, Kosuke Namba

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505 (Japan). yoshi@tokushima-u.ac.jp.

PMID: 24174159
DOI: 10.1002/anie.201306903

Abstract

Radical methods: The title reaction proceeds in the presence of a palladium catalyst to deliver substituted tetrahydrocyclobuta[b]benzofurans in a stereoselective manner. A radical mechanism is discussed.

Keywords: cyclizations; heterocycles; palladium; radicals; synthetic methods.

Publication types

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

MeSH terms

Benzofurans / chemical synthesis*
Benzofurans / chemistry
Carbonates / chemical synthesis
Carbonates / chemistry
Catalysis
Cyclization
Cycloaddition Reaction
Molecular Structure
Oxidation-Reduction
Palladium / chemistry*
Phenols / chemistry*
Stereoisomerism
Vinyl Compounds / chemistry*

Substances

Benzofurans
Carbonates
Phenols
Vinyl Compounds
Palladium