DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline N-oxide

Dinabandhu Barik; Pritishree Panigrahi; Supriya Manna; Nikita Chakraborty; Anushka Phouzder; Bhisma K. Patel

doi:10.1039/d5cc06699a

DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline N-oxide

Dinabandhu Barik
, Pritishree Panigrahi
, Supriya Manna
, Nikita Chakraborty
, Anushka Phouzder
, Bhisma K. Patel

Indian Institute of Technology Delhi

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

Abstract

A visible light-mediated, electron donor–acceptor (EDA) complex-enabled regioselective C4-sulfonylated quinoline N-oxide is presented. In this transformation, organic thiosulfonates serve as a sulfonyl radical (RSO₂˙) precursor, enabling the formation of either C4 sulfonylated quinoline N-oxide or C4 sulfonylated quinoline (deoxygenated) by slight variation of the solvent composition. The base DABCO acts as an electron donor, forming an EDA complex with the acceptor thiosulfonate, generating an RSO₂˙. DABCO also serves as a transient directing group in dictating the C4-regioselectivity by temporarily blocking the more reactive C2 site.

Original language	English
Pages (from-to)	3037-3040
Number of pages	4
Journal	Chemical Communications
Volume	62
Issue number	9
DOIs	https://doi.org/10.1039/d5cc06699a
Publication status	Published - 3 Feb 2026
Externally published	Yes

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title = "DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline N-oxide",

abstract = "A visible light-mediated, electron donor{\textendash}acceptor (EDA) complex-enabled regioselective C4-sulfonylated quinoline N-oxide is presented. In this transformation, organic thiosulfonates serve as a sulfonyl radical (RSO2˙) precursor, enabling the formation of either C4 sulfonylated quinoline N-oxide or C4 sulfonylated quinoline (deoxygenated) by slight variation of the solvent composition. The base DABCO acts as an electron donor, forming an EDA complex with the acceptor thiosulfonate, generating an RSO2˙. DABCO also serves as a transient directing group in dictating the C4-regioselectivity by temporarily blocking the more reactive C2 site.",

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T1 - DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline N-oxide

AU - Barik, Dinabandhu

AU - Panigrahi, Pritishree

AU - Manna, Supriya

AU - Chakraborty, Nikita

AU - Phouzder, Anushka

AU - Patel, Bhisma K.

N1 - Publisher Copyright: This journal is © The Royal Society of Chemistry, 2026

PY - 2026/2/3

Y1 - 2026/2/3

N2 - A visible light-mediated, electron donor–acceptor (EDA) complex-enabled regioselective C4-sulfonylated quinoline N-oxide is presented. In this transformation, organic thiosulfonates serve as a sulfonyl radical (RSO2˙) precursor, enabling the formation of either C4 sulfonylated quinoline N-oxide or C4 sulfonylated quinoline (deoxygenated) by slight variation of the solvent composition. The base DABCO acts as an electron donor, forming an EDA complex with the acceptor thiosulfonate, generating an RSO2˙. DABCO also serves as a transient directing group in dictating the C4-regioselectivity by temporarily blocking the more reactive C2 site.

AB - A visible light-mediated, electron donor–acceptor (EDA) complex-enabled regioselective C4-sulfonylated quinoline N-oxide is presented. In this transformation, organic thiosulfonates serve as a sulfonyl radical (RSO2˙) precursor, enabling the formation of either C4 sulfonylated quinoline N-oxide or C4 sulfonylated quinoline (deoxygenated) by slight variation of the solvent composition. The base DABCO acts as an electron donor, forming an EDA complex with the acceptor thiosulfonate, generating an RSO2˙. DABCO also serves as a transient directing group in dictating the C4-regioselectivity by temporarily blocking the more reactive C2 site.

UR - https://www.scopus.com/pages/publications/105029408880

U2 - 10.1039/d5cc06699a

DO - 10.1039/d5cc06699a

M3 - Article

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AN - SCOPUS:105029408880

SN - 1359-7345

VL - 62

SP - 3037

EP - 3040

JO - Chemical Communications

JF - Chemical Communications

IS - 9

ER -

DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline N-oxide

Abstract

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