375-72-4 | Nonafluorobutanesulfonyl fluoride

CAS:375-72-4 | Nonafluorobutanesulfonyl fluoride ,Description

Nonafluorobutanesulfonyl fluoride (NFBSF) is a fluorinated compound that has become increasingly important in the field of scientific research. It is a powerful reagent for the synthesis of a variety of compounds, and has been used in a range of applications, including drug discovery, protein engineering, and biochemistry. In 
 

Scientific Research Applications

Synthesis of Vinylphosphonates

Nonafluorobutanesulfonyl fluoride has been used in the synthesis of a new class of vinylphosphonates, known as α-phosphonovinyl nonafluorobutanesulfonates (nonaflates). These are prepared from acylphosphonates and nonafluorobutanesulfonyl fluoride in the presence of DBU, and can be converted into phosphono-containing enynes and dienes via palladium-catalyzed coupling reactions (Okauchi et al., 1999).

Stereoselective Synthesis of Alkenyl Nonaflates

Nonafluorobutanesulfonyl fluoride is instrumental in the fluoride-catalyzed reaction with silyl enol ethers for an expedient and stereoselective synthesis of alkenyl nonaflates. This method results in the synthesis of a wide variety of cyclic and acyclic alkenyl nonaflates with good to excellent yields, retaining the E/Z configuration of isomeric alkenes (Lyapkalo et al., 2002).

Palladium-Catalyzed Cross-Coupling of Phenols

Nonafluorobutanesulfonyl fluoride is used in palladium-catalyzed coupling reactions of phenols, such as Suzuki–Miyaura, Sonogashira, Stille, and Buchwald–Hartwig couplings. These reactions proceed through the in situ nonaflation of phenols (Ikawa et al., 2012).

Heck Reactions and Fragmentation of Furan Derivatives

Nonafluorobutanesulfonyl fluoride plays a role in the nonaflation of lithium enolates or silyl enol ethers for the synthesis of ethenyl nonaflate and (Z)-buta-1,3-dien-1-yl nonaflate. These compounds are used in Heck reactions with monosubstituted alkenes to produce coupling products (Lyapkalo et al., 2001).

Transition Metal-Catalyzed Reactions

Nonafluorobutanesulfonyl fluoride is used in various transition metal-catalyzed reactions and typical transformations, offering advantages over commonly used triflates. It is particularly effective in the generation of alkenyl and (het)aryl nonaflates for processes like Heck, Suzuki, Sonogashira, and amination reactions (Hoegermeier & Reissig, 2009).

Dehydrative Glycosylation Protocol

A dehydrative glycosylation protocol mediated by nonafluorobutanesulfonyl fluoride has been developed. This new protocol proceeds under mild basic conditions and results in high yields of symmetrical 1,1’-disaccharides (Tang et al., 2020).

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