Sulfones Bearing Perfluorinated Pyridine Group: Synthesis and Photocatalytic Reaction with α‐(Trifluoromethyl)styrenes

Sulfones Bearing Perfluorinated Pyridine Group: Synthesis and Photocatalytic Reaction with α‐(Trifluoromethyl)styrenes Full article

Journal

Chemcatchem
ISSN: 1867-3899 , E-ISSN: 1867-3880

Output data

Year: 2023, Volume: 15, Number: 12, Article number : e202300505, Pages count : DOI: 10.1002/cctc.202300505

Authors

Savchenko Artem G. ^1,2 , Zubkov Mikhail O. ² , Kokorekin Vladimir A. ² , Hu Jinbo ³ , Dilman Alexander ²

Affiliations

1	Department of Chemistry Moscow State University 119991 Moscow Leninskie Gory 1–3 Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry 119991 Moscow Leninsky prosp. 47 Russian Federation
3	Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 200032 Shanghai 345 Ling-Ling Road China

A photocatalytic protocol for the reductive coupling of tetrafluoropyridyl-substituted sulfones with α-(trifluoromethyl)styrenes in the presence of zinc and sodium iodide is reported. Sulfones were obtained by oxidation of the corresponding sulfides catalyzed by molybdenum or ruthenium salts. A combination of sulfonyl fragment and electron depleting fluorinated pyridyl group is a key feature determined properties of these sulfones. Their propensity to undergo single electron reduction and to form electron donor-acceptor complexes with N-arylamines were evaluated. Plausible pathways of fragmentation of radical anion generated after single electron reduction of sulfones were analyzed, and the pathway leading to the formation of the alkyl radical and the sulfinate anion was found preferable.

Savchenko A.G. , Zubkov M.O. , Kokorekin V.A. , Hu J. , Dilman A.
Sulfones Bearing Perfluorinated Pyridine Group: Synthesis and Photocatalytic Reaction with α‐(Trifluoromethyl)styrenes
Chemcatchem. 2023. V.15. N12. e202300505 . DOI: 10.1002/cctc.202300505 WOS Scopus OpenAlex

Web of science:	WOS:000988864600001
Scopus:	2-s2.0-85159450960
OpenAlex:	W4367312512

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OpenAlex	9
Scopus	7
Web of science	8