A new cycloaddition profile for: Ortho -quinone methides: Photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo [b] cyclopenta [e] oxepines

Kenta Tanaka; Yosuke Asada; Yujiro Hoshino

doi:10.1039/d1cc06332d

A new cycloaddition profile for: Ortho -quinone methides: Photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo [b] cyclopenta [e] oxepines

Kenta Tanaka, Yosuke Asada, Yujiro Hoshino

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction represents a promising tool for the synthesis of natural products and bioactive compounds that contain a benzoxepine structure.

Original language	English
Pages (from-to)	2476-2479
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	15
DOIs	https://doi.org/10.1039/d1cc06332d
Publication status	Published - Feb 21 2022
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc06332d

Cite this

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title = "A new cycloaddition profile for: Ortho -quinone methides: Photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo [b] cyclopenta [e] oxepines",

abstract = "Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction represents a promising tool for the synthesis of natural products and bioactive compounds that contain a benzoxepine structure.",

author = "Kenta Tanaka and Yosuke Asada and Yujiro Hoshino",

note = "Funding Information: This work was supported by Tokuyama Science Foundation, Takahashi Industrial and Economic Research Foundation, Research Foundation for the Electrotechnology of Chubu, The Futaba Foundation, Yashima Environment Technology Foundation, Fukuoka Naohiko Memorial Foundation, Funding Information: The Japan Society for Bioscience, Biotechnology, and Agro-chemistry, The Society of Iodine Science, as well as by JSPS KAKENHI Grant Number JP 20K22537. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

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doi = "10.1039/d1cc06332d",

language = "English",

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journal = "Chemical Communications",

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AU - Tanaka, Kenta

AU - Asada, Yosuke

AU - Hoshino, Yujiro

N1 - Funding Information: This work was supported by Tokuyama Science Foundation, Takahashi Industrial and Economic Research Foundation, Research Foundation for the Electrotechnology of Chubu, The Futaba Foundation, Yashima Environment Technology Foundation, Fukuoka Naohiko Memorial Foundation, Funding Information: The Japan Society for Bioscience, Biotechnology, and Agro-chemistry, The Society of Iodine Science, as well as by JSPS KAKENHI Grant Number JP 20K22537. Publisher Copyright: © The Royal Society of Chemistry.

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N2 - Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction represents a promising tool for the synthesis of natural products and bioactive compounds that contain a benzoxepine structure.

AB - Visible-light-induced [6+4] cycloaddition reactions of ortho-quinone methides have been developed. The reaction of ortho-quinone methides with pentafulvenes in the presence of a thioxanthylium photoredox catalyst afforded benzo[b]cyclopenta[e]oxepines. The present reaction represents a promising tool for the synthesis of natural products and bioactive compounds that contain a benzoxepine structure.

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A new cycloaddition profile for: Ortho -quinone methides: Photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo [b] cyclopenta [e] oxepines

Abstract

ASJC Scopus subject areas

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