Exploratory study of the reaction of bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor™ reagent) with diaryl sulfoxides: Novel routes to Ar2SF2 and Ar2SF(OTf) via sulfoxide activation

Exploratory study of the reaction of bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor™ reagent) with diaryl sulfoxides: Novel routes to Ar2SF2 and Ar2SF(OTf) via sulfoxide activation Научная публикация

Журнал

Journal of Fluorine Chemistry
ISSN: 0022-1139

Вых. Данные

Год: 2002, Том: 115, Номер: 2, Страницы: 169-173 Страниц : 5 DOI: 10.1016/S0022-1139(02)00058-1

Ключевые слова

Bis(2-methoxyethyl)aminosulfur trifluoride; Diaryl sulfoxides; HF/pyridine

Авторы

Laali K.K. , Borodkin G.I.

Организации

1	(Scopus) Department of Chemistry, Kent State University, 44242 Kent, OH, United States
2	(Scopus) Visiting Scientist on leave from Novosibirsk Institute of Organic Chemistry, Russian Federation

Neither bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor™ reagent) nor HF/pyridine alone can fluorinate diaryl sulfoxides. S-fluorination can be effected by activating the sulfoxide via protonation with HF/pyridine (70:30) to form sulfoxonium ions in equilibrium which are then S-fluorinated in situ with Deoxofluor™ to give Ar2SF2 compounds. Conversions depend strongly on steric factors and the reactions require the use of excess Deoxofluor™ and HF/pyridine. NMR data for the resulting diarylsulfur difluorides are gathered and discussed. Sulfoxide activation via diaryl (trifloxy) sulfonium triflate generated in situ from Ar2SO with triflic anhydride at low temperature represents another strategy for S-fluorination with Deoxofluor™ to generate Ar2S(OTf)F. © 2002 Elsevier Science B.V. All rights reserved.

Laali K.K. , Borodkin G.I.
Exploratory study of the reaction of bis(2-methoxyethyl)aminosulfur trifluoride (Deoxofluor™ reagent) with diaryl sulfoxides: Novel routes to Ar2SF2 and Ar2SF(OTf) via sulfoxide activation
Journal of Fluorine Chemistry. 2002. V.115. N2. P.169-173. DOI: 10.1016/S0022-1139(02)00058-1 WOS Scopus РИНЦ

Опубликована в печати:

1 июн. 2002 г.

Web of science	WOS:000176607900012
Scopus	2-s2.0-0037188808
РИНЦ	14234704
OpenAlex	W2146663846