Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels-Alder Reactions

Kenta Tanaka; Mami Kishimoto; Yuta Tanaka; Yusuke Kamiyama; Yosuke Asada; Mayumi Sukekawa; Naoya Ohtsuka; Toshiyasu Suzuki; Norie Momiyama; Kiyoshi Honda; Yujiro Hoshino

doi:10.1021/acs.joc.1c02972

Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels-Alder Reactions

Kenta Tanaka, Mami Kishimoto, Yuta Tanaka, Yusuke Kamiyama, Yosuke Asada, Mayumi Sukekawa, Naoya Ohtsuka, Toshiyasu Suzuki, Norie Momiyama, Kiyoshi Honda, Yujiro Hoshino

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

5 Citations (Scopus)

Abstract

Moderately oxidizing thioxanthylium photoredox catalysts that operate under irradiation with green light have been developed. These catalysts exhibit relatively moderate excited-state reduction potentials [E_1/2(C*/C^•-) = 1.75-1.94 V vs saturated calomel electrode (SCE)] and can efficiently promote radical-cation Diels-Alder reactions under irradiation with green light. Interestingly, β-halogenostyrenes (E_p/2= 1.57-1.61 V vs SCE) are well tolerated, affording synthetically useful halocyclohexenes.

Original language	English
Pages (from-to)	3319-3328
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	87
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.1c02972
Publication status	Published - Mar 4 2022
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c02972

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title = "Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels-Alder Reactions",

abstract = "Moderately oxidizing thioxanthylium photoredox catalysts that operate under irradiation with green light have been developed. These catalysts exhibit relatively moderate excited-state reduction potentials [E1/2(C*/C•-) = 1.75-1.94 V vs saturated calomel electrode (SCE)] and can efficiently promote radical-cation Diels-Alder reactions under irradiation with green light. Interestingly, β-halogenostyrenes (Ep/2= 1.57-1.61 V vs SCE) are well tolerated, affording synthetically useful halocyclohexenes.",

author = "Kenta Tanaka and Mami Kishimoto and Yuta Tanaka and Yusuke Kamiyama and Yosuke Asada and Mayumi Sukekawa and Naoya Ohtsuka and Toshiyasu Suzuki and Norie Momiyama and Kiyoshi Honda and Yujiro Hoshino",

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doi = "10.1021/acs.joc.1c02972",

language = "English",

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T1 - Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels-Alder Reactions

AU - Tanaka, Kenta

AU - Kishimoto, Mami

AU - Tanaka, Yuta

AU - Kamiyama, Yusuke

AU - Asada, Yosuke

AU - Sukekawa, Mayumi

AU - Ohtsuka, Naoya

AU - Suzuki, Toshiyasu

AU - Momiyama, Norie

AU - Honda, Kiyoshi

AU - Hoshino, Yujiro

PY - 2022/3/4

Y1 - 2022/3/4

N2 - Moderately oxidizing thioxanthylium photoredox catalysts that operate under irradiation with green light have been developed. These catalysts exhibit relatively moderate excited-state reduction potentials [E1/2(C*/C•-) = 1.75-1.94 V vs saturated calomel electrode (SCE)] and can efficiently promote radical-cation Diels-Alder reactions under irradiation with green light. Interestingly, β-halogenostyrenes (Ep/2= 1.57-1.61 V vs SCE) are well tolerated, affording synthetically useful halocyclohexenes.

AB - Moderately oxidizing thioxanthylium photoredox catalysts that operate under irradiation with green light have been developed. These catalysts exhibit relatively moderate excited-state reduction potentials [E1/2(C*/C•-) = 1.75-1.94 V vs saturated calomel electrode (SCE)] and can efficiently promote radical-cation Diels-Alder reactions under irradiation with green light. Interestingly, β-halogenostyrenes (Ep/2= 1.57-1.61 V vs SCE) are well tolerated, affording synthetically useful halocyclohexenes.

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DO - 10.1021/acs.joc.1c02972

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

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Moderately Oxidizing Thioxanthylium Organophotoredox Catalysts for Radical-Cation Diels-Alder Reactions

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