Diethylaminodifluorosulfinium tetrafluoroborate

CAS 63517-29-3, Cat. No EN300-393165
Deoxofluorinating reagent and activating agent of some organic groups

Diethylaminodifluorosulfinium Tetrafluoroborate

XtalFluor-E is a powerful and versatile fluorinating agent that surpasses traditional reagents in multiple aspects. XtalFluor-E, a tetrafluoroborate salt, offers several advantages over its renowned precursor, DAST[1]. The salt form exhibits enhanced handling ease and higher temperature stability[2]. As a deoxofluorinating reagent, XtalFluor-E demonstrates superior selectivity compared to SF4 and generates fewer elimination byproducts[3], [4]. Beyond this, XtalFluor-E also serves as an activating reagent for substrates such as alcohols and carboxylic acids, promoting the substitution of oxygen by other nucleophiles like halides or amines[1], [4]. Additionally, it facilitates regioselective aziridine ring opening, leading to the formation of fluorinated diamino acid derivatives.

Synonyms: XtalFluor-E®, (Diethylamino)difluorosulfonium tetrafluoroborate, diethylamino(difluoro)sulfanium;tetrafluoroborate

Selected publication

  1. Diethylaminodifluorosulfinium Tetrafluoroborate (XtalFluor-E®).

    Mahé O.; Paquin J.-F. Encyclopedia of Reagents for Organic Synthesis 2013. DOI: 10.1002/047084289X.rn01631

  2. Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents.

    Beaulieu F.; Beauregard L.-P.; Courchesne G.; Couturier M.; LaFlamme F.; L’Heureux A. Org Lett 2009, 11 (21), 5050–5053. DOI: 10.1021/ol902039q

  3. Synthesis and Chemical Transformations of Diazolyl α,α-Difluoroacetates.

    Geraschenko O. V.; Solomin V. V.; Vashchenko B. V.; Khodakivskyi P.; Tolmachev A. A.; Grygorenko O. O. J Fluor Chem 2020, 229, 109407. DOI: 10.1016/j.jfluchem.2019.109407

  4. A Novel and Selective Fluoride Opening of Aziridines by XtalFluor-E. Synthesis of Fluorinated Diamino Acid Derivatives.

    Nonn M.; Kiss L.; Haukka M.; Fustero S.; Fülöp F. Org Lett 2015, 17 (5), 1074–1077. DOI: 10.1021/acs.orglett.5b00182