Open Access
Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage
Publication type: Journal Article
Publication date: 2024-01-01
scimago Q1
wos Q1
SJR: 2.138
CiteScore: 12.6
Impact factor: 7.4
ISSN: 20416520, 20416539
PubMed ID:
38179514
General Chemistry
Abstract
Carboxylic acids and thiols are basic chemical compounds with diverse utility and widespread reactivity. However, the direct conversion of unprotected acids to thiols is hampered due to a fundamental problem – free thiols are incompatible with the alkyl radicals formed on decarboxylation of carboxylic acids. Herein, we describe a concept for the direct photocatalytic thiolation of unprotected acids allowing unprotected thiols and their derivatives to be obtained. The method is based on the application of a thionocarbonate reagent featuring the N–O bond. The reagent serves both for the rapid trapping of alkyl radicals and for the facile regeneration of the acridine-type photocatalyst.
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Metrics
19
Total citations:
19
Citations from 2025:
13
(68.42%)
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MLA
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GOST
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Lipilin D. L. et al. Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage // Chemical Science. 2024. Vol. 15. No. 2. pp. 644-650.
GOST all authors (up to 50)
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Lipilin D. L., Zubkov M. O., Kosobokov M. D., Dilman A. D. Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage // Chemical Science. 2024. Vol. 15. No. 2. pp. 644-650.
Cite this
RIS
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TY - JOUR
DO - 10.1039/d3sc05513b
UR - https://xlink.rsc.org/?DOI=D3SC05513B
TI - Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage
T2 - Chemical Science
AU - Lipilin, Dmitry L
AU - Zubkov, Mikhail O.
AU - Kosobokov, Mikhail D
AU - Dilman, Alexander D
PY - 2024
DA - 2024/01/01
PB - Royal Society of Chemistry (RSC)
SP - 644-650
IS - 2
VL - 15
PMID - 38179514
SN - 2041-6520
SN - 2041-6539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2024_Lipilin,
author = {Dmitry L Lipilin and Mikhail O. Zubkov and Mikhail D Kosobokov and Alexander D Dilman},
title = {Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage},
journal = {Chemical Science},
year = {2024},
volume = {15},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=D3SC05513B},
number = {2},
pages = {644--650},
doi = {10.1039/d3sc05513b}
}
Cite this
MLA
Copy
Lipilin, Dmitry L., et al. “Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage.” Chemical Science, vol. 15, no. 2, Jan. 2024, pp. 644-650. https://xlink.rsc.org/?DOI=D3SC05513B.
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