Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer

Hirohito Hayashi; Bin Wang; Xiangyang Wu; Shi Jie Teo; Atsushi Kaga; Kohei Watanabe; Ryo Takita; Edwin K.L. Yeow; Shunsuke Chiba

doi:10.1002/adsc.201901601

Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer

Hirohito Hayashi, Bin Wang, Xiangyang Wu, Shi Jie Teo, Atsushi Kaga, Kohei Watanabe, Ryo Takita, Edwin K.L. Yeow^*, Shunsuke Chiba

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.).

Original language	English
Pages (from-to)	2223-2231
Number of pages	9
Journal	Advanced Synthesis and Catalysis
Volume	362
Issue number	11
DOIs	https://doi.org/10.1002/adsc.201901601
Publication status	Published - May 26 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

Anion radicals
Aryl radicals
Cross-coupling
Single-electron-transfer
Visible light

Access to Document

10.1002/adsc.201901601

Cite this

@article{94b62182c5bd4dedbdaef04157830676,

title = "Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer",

abstract = "We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.).",

keywords = "Anion radicals, Aryl radicals, Cross-coupling, Single-electron-transfer, Visible light",

author = "Hirohito Hayashi and Bin Wang and Xiangyang Wu and Teo, {Shi Jie} and Atsushi Kaga and Kohei Watanabe and Ryo Takita and Yeow, {Edwin K.L.} and Shunsuke Chiba",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = may,

day = "26",

doi = "10.1002/adsc.201901601",

language = "English",

volume = "362",

pages = "2223--2231",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "11",

}

TY - JOUR

T1 - Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer

AU - Hayashi, Hirohito

AU - Wang, Bin

AU - Wu, Xiangyang

AU - Teo, Shi Jie

AU - Kaga, Atsushi

AU - Watanabe, Kohei

AU - Takita, Ryo

AU - Yeow, Edwin K.L.

AU - Chiba, Shunsuke

PY - 2020/5/26

Y1 - 2020/5/26

N2 - We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.).

AB - We report a protocol for aryl cross-coupling of electron-deficient aryl halides with electron-rich (hetero)arenes that is driven solely by violet light. This process takes advantage of formation of photo-excited state of electron-deficient aryl halides, that are reduced by electron-rich (hetero)arenes to form a pair of aryl anion and cation radicals. The resulting aryl anion radicals of aryl halides undergo mesolysis of the carbon-halogen bond to generate aryl radicals, that are coupled most likely with aryl cation radicals to afford functionalized biaryls. (Figure presented.).

KW - Anion radicals

KW - Aryl radicals

KW - Cross-coupling

KW - Single-electron-transfer

KW - Visible light

UR - http://www.scopus.com/inward/record.url?scp=85083845486&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85083845486&partnerID=8YFLogxK

U2 - 10.1002/adsc.201901601

DO - 10.1002/adsc.201901601

M3 - Article

AN - SCOPUS:85083845486

SN - 1615-4150

VL - 362

SP - 2223

EP - 2231

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11

ER -

Biaryl Cross-Coupling Enabled by Photo-Induced Electron Transfer

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

Access to Document

Other files and links

Fingerprint

Cite this