Photocatalytic Radical Cascade Dehalogenation/Carbo-cyclization/Sulfonylation Leading to Indole- and Benzofuran-Based Benzylic Sulfones

Qing Quan Liu; Jia Zhuo Li; Yan Jing Wang; Yan Ning Leng; Yu Wen Huang; Xin Chao Meng; Bo Rong Leng; De Cai Wang; Yi Long Zhu

doi:10.1021/acs.joc.3c02068

Photocatalytic Radical Cascade Dehalogenation/Carbo-cyclization/Sulfonylation Leading to Indole- and Benzofuran-Based Benzylic Sulfones

Qing Quan Liu, Jia Zhuo Li, Yan Jing Wang, Yan Ning Leng, Yu Wen Huang, Xin Chao Meng, Bo Rong Leng, De Cai Wang, Yi Long Zhu

School of Pharmaceutical Sciences

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

4 Scopus citations

Abstract

This study presents a convenient approach to the synthesis of indole- and benzofuran-based benzylic sulfones using unactivated alkynes containing aryl iodides and sodium sulfinates under visible light irradiation. The procedure involves a sequential series of dehalogenation, carbo-cyclization, and radical sulfonylation. Plausible insights into the reaction mechanism are derived from control experiments, leading to the proposal of a radical cascade reaction pathway.

Original language	English
Pages (from-to)	17227-17236
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	88
Issue number	24
DOIs	https://doi.org/10.1021/acs.joc.3c02068
State	Published - 15 Dec 2023

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title = "Photocatalytic Radical Cascade Dehalogenation/Carbo-cyclization/Sulfonylation Leading to Indole- and Benzofuran-Based Benzylic Sulfones",

abstract = "This study presents a convenient approach to the synthesis of indole- and benzofuran-based benzylic sulfones using unactivated alkynes containing aryl iodides and sodium sulfinates under visible light irradiation. The procedure involves a sequential series of dehalogenation, carbo-cyclization, and radical sulfonylation. Plausible insights into the reaction mechanism are derived from control experiments, leading to the proposal of a radical cascade reaction pathway.",

author = "Liu, {Qing Quan} and Li, {Jia Zhuo} and Wang, {Yan Jing} and Leng, {Yan Ning} and Huang, {Yu Wen} and Meng, {Xin Chao} and Leng, {Bo Rong} and Wang, {De Cai} and Zhu, {Yi Long}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

month = dec,

day = "15",

doi = "10.1021/acs.joc.3c02068",

language = "英语",

volume = "88",

pages = "17227--17236",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "24",

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TY - JOUR

T1 - Photocatalytic Radical Cascade Dehalogenation/Carbo-cyclization/Sulfonylation Leading to Indole- and Benzofuran-Based Benzylic Sulfones

AU - Liu, Qing Quan

AU - Li, Jia Zhuo

AU - Wang, Yan Jing

AU - Leng, Yan Ning

AU - Huang, Yu Wen

AU - Meng, Xin Chao

AU - Leng, Bo Rong

AU - Wang, De Cai

AU - Zhu, Yi Long

PY - 2023/12/15

Y1 - 2023/12/15

N2 - This study presents a convenient approach to the synthesis of indole- and benzofuran-based benzylic sulfones using unactivated alkynes containing aryl iodides and sodium sulfinates under visible light irradiation. The procedure involves a sequential series of dehalogenation, carbo-cyclization, and radical sulfonylation. Plausible insights into the reaction mechanism are derived from control experiments, leading to the proposal of a radical cascade reaction pathway.

AB - This study presents a convenient approach to the synthesis of indole- and benzofuran-based benzylic sulfones using unactivated alkynes containing aryl iodides and sodium sulfinates under visible light irradiation. The procedure involves a sequential series of dehalogenation, carbo-cyclization, and radical sulfonylation. Plausible insights into the reaction mechanism are derived from control experiments, leading to the proposal of a radical cascade reaction pathway.

UR - http://www.scopus.com/inward/record.url?scp=85179607768&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.3c02068

DO - 10.1021/acs.joc.3c02068

M3 - 文章

AN - SCOPUS:85179607768

SN - 0022-3263

VL - 88

SP - 17227

EP - 17236

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 24

ER -

Photocatalytic Radical Cascade Dehalogenation/Carbo-cyclization/Sulfonylation Leading to Indole- and Benzofuran-Based Benzylic Sulfones

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