Synthesis of Benzo[c]cinnolinium Salts from 2-Azobiaryls by Copper(II) or Electrochemical Oxidation

Huan Chang Hsiao; Meng Che Li; Guganchandar Vedarethinam; Pei Lin Chen; Shih Ching Chuang

doi:10.1021/acs.orglett.4c00213

Synthesis of Benzo[c]cinnolinium Salts from 2-Azobiaryls by Copper(II) or Electrochemical Oxidation

Huan Chang Hsiao, Meng Che Li, Guganchandar Vedarethinam, Pei Lin Chen, Shih Ching Chuang^*

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Synthesis of benzo[c]cinnolinium salts by copper(II)-promoted or electrochemical oxidation of 2-azobiaryls is described. A variety of diversely functionalized benzo[c]cinnolinium salts were easily constructed by this strategy with excellent functional group tolerance and high efficiency. An interesting fluorescence centered at 571 nm is revealed by a benzo[c]cinnolinium salt with electron push-pull substitutions. The mechanism is proposed to go through single-electron transfer driven by oxidant and intramolecular cyclization via nucleophilic addition, followed by an anion exchange.

原文	English
頁（從 - 到）	1694-1698
頁數	5
期刊	Organic Letters
卷	26
發行號	8
DOIs	https://doi.org/10.1021/acs.orglett.4c00213
出版狀態	Published - 1 3月 2024

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10.1021/acs.orglett.4c00213

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@article{9f229efe0e734b68b8d423ce390825e3,

title = "Synthesis of Benzo[c]cinnolinium Salts from 2-Azobiaryls by Copper(II) or Electrochemical Oxidation",

abstract = "Synthesis of benzo[c]cinnolinium salts by copper(II)-promoted or electrochemical oxidation of 2-azobiaryls is described. A variety of diversely functionalized benzo[c]cinnolinium salts were easily constructed by this strategy with excellent functional group tolerance and high efficiency. An interesting fluorescence centered at 571 nm is revealed by a benzo[c]cinnolinium salt with electron push-pull substitutions. The mechanism is proposed to go through single-electron transfer driven by oxidant and intramolecular cyclization via nucleophilic addition, followed by an anion exchange.",

author = "Hsiao, {Huan Chang} and Li, {Meng Che} and Guganchandar Vedarethinam and Chen, {Pei Lin} and Chuang, {Shih Ching}",

note = "Publisher Copyright: {\textcopyright} 2024 The Authors. Published by American Chemical Society",

year = "2024",

month = mar,

day = "1",

doi = "10.1021/acs.orglett.4c00213",

language = "English",

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T1 - Synthesis of Benzo[c]cinnolinium Salts from 2-Azobiaryls by Copper(II) or Electrochemical Oxidation

AU - Hsiao, Huan Chang

AU - Li, Meng Che

AU - Vedarethinam, Guganchandar

AU - Chen, Pei Lin

AU - Chuang, Shih Ching

PY - 2024/3/1

Y1 - 2024/3/1

N2 - Synthesis of benzo[c]cinnolinium salts by copper(II)-promoted or electrochemical oxidation of 2-azobiaryls is described. A variety of diversely functionalized benzo[c]cinnolinium salts were easily constructed by this strategy with excellent functional group tolerance and high efficiency. An interesting fluorescence centered at 571 nm is revealed by a benzo[c]cinnolinium salt with electron push-pull substitutions. The mechanism is proposed to go through single-electron transfer driven by oxidant and intramolecular cyclization via nucleophilic addition, followed by an anion exchange.

AB - Synthesis of benzo[c]cinnolinium salts by copper(II)-promoted or electrochemical oxidation of 2-azobiaryls is described. A variety of diversely functionalized benzo[c]cinnolinium salts were easily constructed by this strategy with excellent functional group tolerance and high efficiency. An interesting fluorescence centered at 571 nm is revealed by a benzo[c]cinnolinium salt with electron push-pull substitutions. The mechanism is proposed to go through single-electron transfer driven by oxidant and intramolecular cyclization via nucleophilic addition, followed by an anion exchange.

UR - http://www.scopus.com/inward/record.url?scp=85185591161&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.4c00213

DO - 10.1021/acs.orglett.4c00213

M3 - Article

C2 - 38360059

AN - SCOPUS:85185591161

SN - 1523-7060

VL - 26

SP - 1694

EP - 1698

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Synthesis of Benzo[c]cinnolinium Salts from 2-Azobiaryls by Copper(II) or Electrochemical Oxidation

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