Visible‐Light‐Promoted Reversible Sulfide/Iodide Exchange in Fluoroalkyl Sulfides Enabled by Electron Donor‐Acceptor Complex Formation

Visible‐Light‐Promoted Reversible Sulfide/Iodide Exchange in Fluoroalkyl Sulfides Enabled by Electron Donor‐Acceptor Complex Formation Full article

Journal

ChemPhotoChem
ISSN: 2367-0932

Output data

Year: 2021, Volume: 5, Number: 6, Pages: 565-570 Pages count : 6 DOI: 10.1002/cptc.202100042

Authors

van der Worp Boris A. ^1,2 , Kosobokov Mikhail D. ¹ , Dilman Alexander D. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation
2	Lomonosov Moscow State University Department of Chemistry 119991 Moscow Leninskie Gory 1–3 Russian Federation

Catalyst-free visible-light-mediated exchange of two photoredox active groups, a 4-perfluoropyridinylthio group and an iodide group, attached to a fluorinated alkyl fragment is described. The reaction can be preparatively performed in both directions by appropriate choice of wavelength, solvent, and counterion. In the forward reaction, alkyl sulfide interacts with an iodide anion to give alkyl iodide and a thiolate anion, with the driving force provided by blue light (455 nm). In the backward process, fluorinated alkyl iodide interacts with the thiolate under violet light (400 nm). The reactions proceed through the formation of electron donor-acceptor (EDA) complexes, which were observed by UV/Vis absorption or NMR spectroscopies. Evidence of the sulfur–iodide interaction was supported by X-ray analysis.

van der Worp B.A. , Kosobokov M.D. , Dilman A.D.
Visible‐Light‐Promoted Reversible Sulfide/Iodide Exchange in Fluoroalkyl Sulfides Enabled by Electron Donor‐Acceptor Complex Formation
ChemPhotoChem. 2021. V.5. N6. P.565-570. DOI: 10.1002/cptc.202100042 WOS Scopus OpenAlex

Web of science:	WOS:000625173700001
Scopus:	2-s2.0-85106511108
OpenAlex:	W3131194820

DB	Citing
OpenAlex	11
Scopus	11
Web of science	11