A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes

A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes Full article

Journal

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

Output data

Year: 2020, Volume: 11, Number: 3, Pages: 737-741 Pages count : 5 DOI: 10.1039/c9sc04643g

Authors

Zubkov Mikhail O. ^1,2 , Kosobokov Mikhail D. ¹ , Levin Vitalij V. ¹ , Kokorekin Vladimir A. ^1,3 , Korlyukov Alexander A. ^4,5 , Hu Jinbo ⁶ , Dilman Alexander D. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
2	Higher Chemical College, D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya sq., 125047 Moscow, Russia
3	I. M. Sechenov First Moscow State Medical University, 8-2 Trubetskaya st., 119991 Moscow, Russia
4	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova st., 119991 Moscow, Russia
5	Pirogov Russian National Research Medical University, 1 Ostrovitianov st., 117997 Moscow, Russia
6	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, 345 Ling-Ling Road, 200032 Shanghai, China

A 4-tetrafluoropyridinylthio group was suggested as a new photoredox-active moiety. The group can be directly installed on difluorostyrenes in a single step by the thiolene click reaction. It proceeds upon visible light catalysis with 9-phenylacridine providing various difluorinated sulfides as radical precursors. Single electron reduction of the C–S bond with the formation of fluoroalkyl radicals is enabled by the electron-poor azine ring. The intermediate difluorinated sulfides were involved in a series of photoredox reactions with silyl enol ethers, alkenes, nitrones and an alkenyl trifluoroborate.

Zubkov M.O. , Kosobokov M.D. , Levin V.V. , Kokorekin V.A. , Korlyukov A.A. , Hu J. , Dilman A.D.
A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes
Chemical Science. 2020. V.11. N3. P.737-741. DOI: 10.1039/c9sc04643g WOS Scopus OpenAlex

Web of science:	WOS:000508917000010
Scopus:	2-s2.0-85078518346
OpenAlex:	W2990348069

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OpenAlex	86
Scopus	76
Web of science	71