133745-75-2 Usage
Description
N-Fluorobenzenesulfonimide (NFSi) is a versatile and commonly used electrophilic fluorinating agent in organic synthesis. It is an off-white to light brown crystalline powder that is effective in introducing fluorine into neutral organic molecules and fluorinating nucleophilic substrates, such as reactive organometallic species and malonate anions. NFSi can be synthesized by the reaction of benzenesulfonimide with fluorine.
Uses
Used in Organic Synthesis:
N-Fluorobenzenesulfonimide is used as a fluorinating reagent for the fluorination of aryls, enolates, carbanions, and organolithiums. It is particularly effective in high-yield fluorination reactions.
Used in Asymmetric Fluorination:
In the presence of a Pd-BINAP catalyst system at room temperature in an ionic liquid, NFSi is used as a fluorinating agent for asymmetric fluorinations.
Used in Enantioselective Fluorination:
N-Fluorobenzenesulfonimide is employed in a palladium-catalyzed enantioselective fluorination of t-butoxycarbonyl lactones and lactams, contributing to the production of chiral molecules with a single enantiomer.
Used in Diastereoselective Fluorination:
NFSi is used for diastereoselective fluorination of Li enolates of chiral carboximides, which is crucial for the synthesis of complex organic molecules with specific stereochemistry.
Used in Directed Fluorination:
N-Fluorobenzenesulfonimide is utilized for directed fluorination of ortho-lithiated aromatics, allowing for the selective introduction of fluorine atoms at desired positions in the molecule.
Used in Electrophilic Difluorination:
NFSi is also used in the electrophilic difluorination of dihalopyridines with butyl lithium, enabling the synthesis of various difluorinated compounds.
Used in Conversion of Alcohols:
N-Fluorobenzenesulfonimide is employed in the direct conversion of alcohols to dibenzenesulfonamides with triphenylphosphine, providing a straightforward route to synthesize these compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 133745-75-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,3,7,4 and 5 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 133745-75:
(8*1)+(7*3)+(6*3)+(5*7)+(4*4)+(3*5)+(2*7)+(1*5)=132
132 % 10 = 2
So 133745-75-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H4F6O2/c10-8(11,12)5-2-1-4(7(16)17)3-6(5)9(13,14)15/h1-3H,(H,16,17)
133745-75-2Relevant articles and documents
Comparative studies on the enantioselective fluorination of oxindoles with structurally modified N-fluorobenzenesulfonimides
Zhang, Yan,Yang, Xian-Jin,Xie, Tian,Chen, Guan-Long,Zhu, Wen-Hua,Zhang, Xiao-Qi,Yang, Xue-Yan,Wu, Xin-Yan,He, Xiao-Peng,He, Hao-Ming
, p. 4933 - 4937 (2013/07/25)
Structurally modified N-fluorobenzenesulfonimides (NFSIs) have been used to study the enantioselective fluorination of oxindoles in the presence of a bis-cinchona alkaloid, (DHQD)2PHAL, as the catalyst. We observe that the NFSI analogues bearin
Method for preparing N-fluorosulfonimides
-
, (2008/06/13)
The present invention relates to a process of preparing N-benzenesulfonimides comprising reacting an alkali metal salt of a sulfonimide with fluorine in the presence of water or water/organic solvent mixtures. N-fluorosulfonimides are useful as fluorinati