Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers

Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2019, Volume: 84, Number: 23, Pages: 15745-15753 Pages count : 9 DOI: 10.1021/acs.joc.9b02478

Authors

Zemtsov Artem A. ¹ , Ashirbaev Salavat S. ¹ , Levin Vitalij V. ¹ , Kokorekin Vladimir A. ^1,2 , Korlyukov Alexander A. ^3,4 , Dilman Alexander D. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation
2	Sechenov First Moscow State Medical University, Trubetskaya st. 8-2, 119991 Moscow, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilov str. 28, 119991 Moscow, Russian Federation
4	N. I. Pirogov Russian National Research Medical University, Ostrovitianov str. 1, 117997 Moscow, Russian Federation

A method for the generation of free radicals from thiazolinium salts upon photocatalytic reduction is described. The thiazolinium salts are generated by treatment with methyl triflate of 2-mercaptothiazolines, which can be readily obtained from alkyl bromides and tosylates via a nucleophilic substitution reaction or by hydrothiolation of alkenes. Silyl enol ethers were used to trap the radicals, furnishing ketones after successive single-electron oxidation and elimination of the silyl cation.

Zemtsov A.A. , Ashirbaev S.S. , Levin V.V. , Kokorekin V.A. , Korlyukov A.A. , Dilman A.D.
Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers
Journal of Organic Chemistry. 2019. V.84. N23. P.15745-15753. DOI: 10.1021/acs.joc.9b02478 WOS Scopus OpenAlex

Web of science:	WOS:000502170600071
Scopus:	2-s2.0-85075552762
OpenAlex:	W2983342871

DB	Citing
OpenAlex	13
Scopus	12
Web of science	12