Hypervalent Sulfur Derivatives as Sulfenylating Reagents: Visible-Light-Mediated Direct Thiolation of Activated C(sp2)–H Bonds with Dihalosulfuranes

Hypervalent Sulfur Derivatives as Sulfenylating Reagents: Visible-Light-Mediated Direct Thiolation of Activated C(sp2)–H Bonds with Dihalosulfuranes Full article

Journal

Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052

Output data

Year: 2024, Volume: 26, Number: 20, Pages: 4323-4328 Pages count : 6 DOI: 10.1021/acs.orglett.4c01305

Authors

Kuznetsova Elizaveta A. ^1,2 , Rysaeva Regina R. ³ , Smolobochkin Andrey V. ¹ , Gazizov Almir S. ¹ , Gerasimova Tatyana P. ¹ , Gerasimova Daria P. ¹ , Lodochnikova Olga A. ¹ , Morozov Vladimir I. ¹ , Vatsadze Sergey Z. ⁴ , Burilov Alexander R. ¹ , Pudovik Michail A. ¹

Affiliations

1	Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova Street 8, Kazan 420088, Russian Federation
2	Kazan National Research Technological University, Karla Marksa Street 68, Kazan 420015, Russian Federation
3	Organic Chemistry Department, Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya 18, Kazan 420008, Russian Federation
4	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russian Federation

In contrast to hypervalent iodine compounds, the chemistry of their sulfur analogues has been considerably less explored. Herein, we report the direct C–H bond thiolation of electron-rich heterocycles, arenes, and 1,3-dicarbonyls by dichlorosulfuranes under mild conditions. Mechanistic studies and density functional theory calculations suggest the radical chain mechanism of the disclosed transformation. The key to success is attributed to a strikingly low S–Cl bond dissociation energy, which enables the generation of radical species upon exposure to daylight.

Kuznetsova E.A. , Rysaeva R.R. , Smolobochkin A.V. , Gazizov A.S. , Gerasimova T.P. , Gerasimova D.P. , Lodochnikova O.A. , Morozov V.I. , Vatsadze S.Z. , Burilov A.R. , Pudovik M.A.
Hypervalent Sulfur Derivatives as Sulfenylating Reagents: Visible-Light-Mediated Direct Thiolation of Activated C(sp2)–H Bonds with Dihalosulfuranes
Organic Letters. 2024. V.26. N20. P.4323-4328. DOI: 10.1021/acs.orglett.4c01305 WOS Scopus OpenAlex

Web of science:	WOS:001224846300001
Scopus:	2-s2.0-85192846745
OpenAlex:	W4396779908

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OpenAlex	2
Scopus	2
Web of science	3