Synthesis of Fused and Linked Benzofurans from 2-Alkynylphenol Derivatives through Rhodium(I)-catalyzed Domino-type Addition Reactions
Keywords:Asymmetric reaction, Benzofuran, Cyclization, Domino reaction, Rhodium
AbstractA 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.
How to Cite
T. Matsuda, S. Abe, H. Ito, T. Tsuboi, H. Kirikae, M. Murakami, Chimia 2018, 72, 888, DOI: 10.2533/chimia.2018.888.
Copyright (c) 2018 Swiss Chemical Society
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.