Green-light-driven thioxanthylium-based organophotoredox catalysts: Organophotoredox promoted radical cation Diels-Alder reaction

Kenta Tanaka; Mami Kishimoto; Mayumi Sukekawa; Yujiro Hoshino; Kiyoshi Honda

doi:10.1016/j.tetlet.2018.07.058

Green-light-driven thioxanthylium-based organophotoredox catalysts: Organophotoredox promoted radical cation Diels-Alder reaction

Kenta Tanaka, Mami Kishimoto, Mayumi Sukekawa, Yujiro Hoshino, Kiyoshi Honda

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

26 Citations (Scopus)

Abstract

Thioxanthylium-based organophotoredox catalysts that operate under irradiation with green light have been developed. These catalysts present high excited-state reduction potentials (E₀′(C^∗/C⁻) = +1.79–1.94 V vs SCE). They are able to efficiently activate dienophiles under green or blue light irradiation afforded the targeted radical cation Diels-Alder cycloadducts in good yields. The present thioxanthylium-based catalysts provide a new green-light-driven photoredox catalysis system.

Original language	English
Pages (from-to)	3361-3364
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2018.07.058
Publication status	Published - Sept 5 2018
Externally published	Yes

Keywords

Green light
Organophotoredox catalyst
Radical cation Diels-Alder reaction
Thioxanthylium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2018.07.058

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title = "Green-light-driven thioxanthylium-based organophotoredox catalysts: Organophotoredox promoted radical cation Diels-Alder reaction",

abstract = "Thioxanthylium-based organophotoredox catalysts that operate under irradiation with green light have been developed. These catalysts present high excited-state reduction potentials (E0′(C∗/C−) = +1.79–1.94 V vs SCE). They are able to efficiently activate dienophiles under green or blue light irradiation afforded the targeted radical cation Diels-Alder cycloadducts in good yields. The present thioxanthylium-based catalysts provide a new green-light-driven photoredox catalysis system.",

keywords = "Green light, Organophotoredox catalyst, Radical cation Diels-Alder reaction, Thioxanthylium",

author = "Kenta Tanaka and Mami Kishimoto and Mayumi Sukekawa and Yujiro Hoshino and Kiyoshi Honda",

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year = "2018",

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TY - JOUR

T1 - Green-light-driven thioxanthylium-based organophotoredox catalysts

T2 - Organophotoredox promoted radical cation Diels-Alder reaction

AU - Tanaka, Kenta

AU - Kishimoto, Mami

AU - Sukekawa, Mayumi

AU - Hoshino, Yujiro

AU - Honda, Kiyoshi

PY - 2018/9/5

Y1 - 2018/9/5

N2 - Thioxanthylium-based organophotoredox catalysts that operate under irradiation with green light have been developed. These catalysts present high excited-state reduction potentials (E0′(C∗/C−) = +1.79–1.94 V vs SCE). They are able to efficiently activate dienophiles under green or blue light irradiation afforded the targeted radical cation Diels-Alder cycloadducts in good yields. The present thioxanthylium-based catalysts provide a new green-light-driven photoredox catalysis system.

AB - Thioxanthylium-based organophotoredox catalysts that operate under irradiation with green light have been developed. These catalysts present high excited-state reduction potentials (E0′(C∗/C−) = +1.79–1.94 V vs SCE). They are able to efficiently activate dienophiles under green or blue light irradiation afforded the targeted radical cation Diels-Alder cycloadducts in good yields. The present thioxanthylium-based catalysts provide a new green-light-driven photoredox catalysis system.

KW - Green light

KW - Organophotoredox catalyst

KW - Radical cation Diels-Alder reaction

KW - Thioxanthylium

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Green-light-driven thioxanthylium-based organophotoredox catalysts: Organophotoredox promoted radical cation Diels-Alder reaction

Abstract

Keywords

ASJC Scopus subject areas

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