Nonafluorobutanesulfonyl фторид

Химические свойства

Nonafluorobutanesulfonyl fluoride is a colorless, volatile liquid that is immiscible with water but soluble in common organic solvents. It is prepared by the electrochemical fluorination of sulfolane.

Использование

Nonafluorobutanesulfonyl fluoride can be used as a general-purpose diazotransfer reagent with high efficiency, wide substrate range, good shelf stability, relatively low cost, and easy purification. It is a favourable alternative to other commonly used diazotransfer reagents^[1]. In addition, Nonafluorobutanesulfonyl fluoride was used in the formation of a new dehydrated glycosylation scheme. In contrast to the main classical glycosylation reactions, this scheme glycosylation reaction is carried out under mildly alkaline conditions. In the absence of an external acceptor, the glycosyl hemiacetal undergoes self-condensation, providing the corresponding symmetric 1,1'- disaccharide in high yield^[2].

Использование

Benzynes were generated from o-(trimethylsilyl) phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process.Nonafluorobutanesulfonyl fluoride (nonaflyl fluoride, C 4 F 9 SO 2 F, NfF) is the most widely used commercially available reagent for the synthesis of nonaflates.

прикладной

Perfluoro-1-butanesulfonyl fluoride (NfF) reacts with alcohols, including phenols, to yield nonafluorobutanesulfonate esters (nonaflates). Nonaflates can be used as electrophiles in several palladium-catalyzed cross coupling reactions and in Buchwald-Hartwig amination. NfF can also be used to prepare aryl nonaflates by reacting with corresponding aryloxysilanes in the presence of fluoride ion.

хранилище

Store in amber colored bottles protected from light; for prolonged storage, PVC bottles are recommended.

использованная литература

[1] JOSE LUIS CHIARA; José R S. Synthesis of α-Diazo Carbonyl Compounds with the Shelf-Stable Diazo Transfer Reagent Nonafluorobutanesulfonyl Azide[J]. Advanced Synthesis & Catalysis, 2011. DOI:10.1002/adsc.201000846.
[2] YU TANG; Biao Y; D Prabhakar Reddy. A dehydrative glycosylation protocol mediated by nonafluorobutanesulfonyl fluoride (NfF)[J]. Tetrahedron, 2021. DOI:10.1016/j.tet.2020.131800.