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

Authors

  • Takanori Matsuda Department of Applied Chemistry Tokyo University of Science 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan;, Email: mtd@rs.tus.ac.jp
  • Shinya Abe Department of Applied Chemistry Tokyo University of Science 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
  • Hirotaka Ito Department of Applied Chemistry Tokyo University of Science 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
  • Tomoya Tsuboi Department of Synthetic Chemistry and Biological Chemistry Kyoto University Katsura, Kyoto 615-8510, Japan
  • Haruki Kirikae Department of Applied Chemistry Tokyo University of Science 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
  • Masahiro Murakami Department of Synthetic Chemistry and Biological Chemistry Kyoto University Katsura, Kyoto 615-8510, Japan;, Email: murakami@sbchem.kyoto-u.ac.jp

DOI:

https://doi.org/10.2533/chimia.2018.888

Keywords:

Asymmetric reaction, Benzofuran, Cyclization, Domino reaction, Rhodium

Abstract

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.

Downloads

Published

2018-12-19

How to Cite

[1]
T. Matsuda, S. Abe, H. Ito, T. Tsuboi, H. Kirikae, M. Murakami, Chimia 2018, 72, 888, DOI: 10.2533/chimia.2018.888.