Work

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

Year: 2018

Type: article

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.

Source: CHIMIA International Journal for Chemistry

DOI: 10.2533/chimia.2018.888

Authors: Takanori Matsuda, Shinya Abe, Hirotaka Ito, Tomoya Tsuboi, Haruki Kirikae, Masahiro Murakami

Institutions: Tokyo University of Science, Kyoto University

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Sumitomo Foundation, Kurata Memorial Hitachi Science and Technology Foundation, Japan Society for the Promotion of Science

Awards: Development of transformations of bicyclic compounds to monocyclic compounds through sequential bond cleavage, Successive construction of cyclic skeletons via migration of transition metals, Development of catalytic transformations that include multiple bond cleavages and formations