Palladium-Catalyzed Intramolecular Migratory Cycloisomerization of 3-Phenoxy Acrylic Acid Ester via C–O Bond Cleavage and C–O/C–C Bonds Formation for 2,3-Disubstituted Benzofurans Synthesis

Migratory cycloisomerization using transition metal catalyst is useful for synthesizing substituted heterocyclic compounds. We achieved palladium-catalyzed migratory cycloisomerization of 3-o-alkynylphenoxy acrylic acid ester derivatives to give 2,3-disubstituted benzofurans. Although there are seve...

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Published inChemical & pharmaceutical bulletin Vol. 71; no. 2; pp. 93 - 100
Main Authors Kuboki, Yuichi, Ohno, Shohei, Sako, Makoto, Murai, Kenichi, Arisawa, Mitsuhiro
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 01.02.2023
Japan Science and Technology Agency
Subjects
Acrylic acid
Benzofuran
Benzofurans - chemistry
bond cleavage
Catalysis
Catalysts
Chemical synthesis
Cleavage
Covalent bonds
cycloisomerization
Heterocyclic Compounds
Isomerization
Palladium
Palladium - chemistry
Propargyl groups
Transition metals
palladium
benzofuran
bond cleavage
cycloisomerization
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Summary:Migratory cycloisomerization using transition metal catalyst is useful for synthesizing substituted heterocyclic compounds. We achieved palladium-catalyzed migratory cycloisomerization of 3-o-alkynylphenoxy acrylic acid ester derivatives to give 2,3-disubstituted benzofurans. Although there are several reports of benzofuran synthesis with palladium-catalyzed migratory cycloisomerization, migratory groups are limited to allyl and propargyl groups. This report is the first example of benzofuran synthesis with palladium-catalyzed cycloisomerization of C(sp2)-O bond cleavage.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c22-00555