Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO2)2 and Thianthrenium Salts

Xin Yuan; Jie Liu; Long Zhou Qin; Xiu Duan; Jian Wang; Meng Yu Wu; Jiang Kai Qiu; Kai Guo

doi:10.1002/adsc.202201294

Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO₂)₂ and Thianthrenium Salts

Xin Yuan, Jie Liu, Long Zhou Qin, Xiu Duan, Jian Wang, Meng Yu Wu, Jiang Kai Qiu, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

11 Scopus citations

Abstract

A direct, visible-light-mediated, radical-cascade addition/sulfonylation/cyclization reaction with DABCO ⋅ (SO₂)₂ and thianthrenium salts is reported herein. This protocol provides operationally-convenient access to various sulfonated functionalized indole [2,1-a] isoquinolines under mild conditions. This transformation features high functional-group tolerance, operational ease, and broad substrate scope. Preliminary studies reveal that the method undergoes a radical pathway. (Figure presented.).

Original language	English
Pages (from-to)	555-567
Number of pages	13
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	4
DOIs	https://doi.org/10.1002/adsc.202201294
State	Published - 21 Feb 2023

Keywords

cyclization
radical-cascade addition
sulfonylation
visible-light-mediated

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10.1002/adsc.202201294

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Yuan, X., Liu, J., Qin, L. Z., Duan, X., Wang, J., Wu, M. Y., Qiu, J. K., & Guo, K. (2023). Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO₂)₂ and Thianthrenium Salts. Advanced Synthesis and Catalysis, 365(4), 555-567. https://doi.org/10.1002/adsc.202201294

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title = "Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO2)2 and Thianthrenium Salts",

abstract = "A direct, visible-light-mediated, radical-cascade addition/sulfonylation/cyclization reaction with DABCO ⋅ (SO2)2 and thianthrenium salts is reported herein. This protocol provides operationally-convenient access to various sulfonated functionalized indole [2,1-a] isoquinolines under mild conditions. This transformation features high functional-group tolerance, operational ease, and broad substrate scope. Preliminary studies reveal that the method undergoes a radical pathway. (Figure presented.).",

keywords = "cyclization, radical-cascade addition, sulfonylation, visible-light-mediated",

author = "Xin Yuan and Jie Liu and Qin, {Long Zhou} and Xiu Duan and Jian Wang and Wu, {Meng Yu} and Qiu, {Jiang Kai} and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = feb,

day = "21",

doi = "10.1002/adsc.202201294",

language = "英语",

volume = "365",

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Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO₂)₂ and Thianthrenium Salts. / Yuan, Xin; Liu, Jie; Qin, Long Zhou et al.
In: Advanced Synthesis and Catalysis, Vol. 365, No. 4, 21.02.2023, p. 555-567.

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

TY - JOUR

T1 - Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO2)2 and Thianthrenium Salts

AU - Yuan, Xin

AU - Liu, Jie

AU - Qin, Long Zhou

AU - Duan, Xiu

AU - Wang, Jian

AU - Wu, Meng Yu

AU - Qiu, Jiang Kai

AU - Guo, Kai

PY - 2023/2/21

Y1 - 2023/2/21

N2 - A direct, visible-light-mediated, radical-cascade addition/sulfonylation/cyclization reaction with DABCO ⋅ (SO2)2 and thianthrenium salts is reported herein. This protocol provides operationally-convenient access to various sulfonated functionalized indole [2,1-a] isoquinolines under mild conditions. This transformation features high functional-group tolerance, operational ease, and broad substrate scope. Preliminary studies reveal that the method undergoes a radical pathway. (Figure presented.).

AB - A direct, visible-light-mediated, radical-cascade addition/sulfonylation/cyclization reaction with DABCO ⋅ (SO2)2 and thianthrenium salts is reported herein. This protocol provides operationally-convenient access to various sulfonated functionalized indole [2,1-a] isoquinolines under mild conditions. This transformation features high functional-group tolerance, operational ease, and broad substrate scope. Preliminary studies reveal that the method undergoes a radical pathway. (Figure presented.).

KW - cyclization

KW - radical-cascade addition

KW - sulfonylation

KW - visible-light-mediated

UR - http://www.scopus.com/inward/record.url?scp=85147365708&partnerID=8YFLogxK

U2 - 10.1002/adsc.202201294

DO - 10.1002/adsc.202201294

M3 - 文章

AN - SCOPUS:85147365708

SN - 1615-4150

VL - 365

SP - 555

EP - 567

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 4

ER -

Synthesis of Alkylsulfonyl-Substituted Indolo[2,1-a]Isoquinolines via Photoredox-Catalyzed Radical-Cascade Addition/Sulfonylation/Cyclization with DABCO ⋅ (SO₂)₂ and Thianthrenium Salts

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