Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage

Direct conversion of carboxylic acids to free thiols via radical relay acridine photocatalysis enabled by N–O bond cleavage Full article

Journal

Chemical Science
ISSN: 2041-6520 , E-ISSN: 2041-6539

Output data

Year: 2024, Volume: 15, Number: 2, Pages: 644-650 Pages count : 7 DOI: 10.1039/d3sc05513b

Authors

Lipilin Dmitry L ¹ , Zubkov Mikhail O ¹ , Kosobokov Mikhail ¹ , Dilman Alexander ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prosp. 47, 119991 Moscow, Russian Federation

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.

Lipilin D.L. , Zubkov M.O. , Kosobokov M. , Dilman A.
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

Web of science:	WOS:001123261000001
Scopus:	2-s2.0-85179823242
OpenAlex:	W4389352472

DB	Citing
OpenAlex	8
Scopus	5
Web of science	8