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Synthesis of Fused and Linked Benzofurans from 2-Alkynylphenol Derivatives through Rhodium(I)-catalyzed Domino-type Addition Reactions

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A rhodium(I)-catalyzed domino-type sequential 5-endo/5-exo cyclization reaction of [(2-acylphenyl) ethynyl]phenols produces indene/benzofuran-fused alcohols. A moderate asymmetric induction is observed when chiral diphosphine ligands are used for rhodium. Indene/indole-fused compounds are synthesized by a similar reaction of [(2-acetylphenyl)ethynyl]anilines. The domino-type 5-endo/5-exo cyclization reaction is extended to substrates having two phenolic hydroxy groups. A linearly-fused array of five- and six-membered rings is constructed. Fused and linked benzofurans possessing 2-cyanoethyl side chains are also synthesized through sequential formation of C–O and C–C bonds.
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Keywords: ASYMMETRIC REACTION; BENZOFURAN; CYCLIZATION; DOMINO REACTION; RHODIUM

Document Type: Research Article

Affiliations: 1: Department of Applied Chemistry Tokyo University of Science 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan;, Email: [email protected] 2: Department of Applied Chemistry Tokyo University of Science 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan 3: Department of Synthetic Chemistry and Biological Chemistry Kyoto University Katsura, Kyoto 615-8510, Japan 4: Department of Synthetic Chemistry and Biological Chemistry Kyoto University Katsura, Kyoto 615-8510, Japan;, Email: [email protected]

Publication date: 01 December 2018

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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