Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage Full article
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Chemical Science
ISSN: 2041-6520 , E-ISSN: 2041-6539 |
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| Output data | Year: 2024, Volume: 15, Number: 2, Pages: 644-650 Pages count : 7 DOI: 10.1039/d3sc05513b | ||
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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.
Cite:
Dmitry L Lipilin
, Mikhail O Zubkov
, Mikhail Kosobokov
, Alexander Dilman
Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage
Chemical Science. 2024. V.15. N2. P.644-650. DOI: 10.1039/d3sc05513b WOS Scopus OpenAlex
Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage
Chemical Science. 2024. V.15. N2. P.644-650. DOI: 10.1039/d3sc05513b WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:001123261000001 |
| Scopus: | 2-s2.0-85179823242 |
| OpenAlex: | W4389352472 |