1-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) as a new, effective reagent for selective fluorofunctionalisation of alkenes under mild reaction conditions

The chemistry of organohalogenic molecules. Part 172. Kinetic studies of bromine transfer from N-bromo-succinimide to norbornene under protic conditions

“…7,8 Halogen transfer from the N type of reagents is very sensitive to reaction conditions, especially in the case of fluorine transfer where acetonitrile as solvent affects the reactions to form Ritter type fluoroamides, whereas in the presence of a nucleophile vicinal fluoro-hydroxy or fluoro-alkoxy products are formed. [25][26][27][28] In order to obtain kinetic and thermodynamic activation information comparable to that on fluorine transfer, 29 we decided first to investigate the products formed in bromination of norbornene with NBS in acetonitrile in the presence of water. From the crude reaction mixture, three main products were isolated by preparative GC, and their structure confirmed by comparison of the spectroscopic data with the literature.…”

Microwave fluorination: a novel, rapid approach to fluorination with Selectfluor®

“…We have shown that microwave conditions are readily applicable to the fluorination of aromatic molecules, when a suitable electrophilic fluorination agent is used such as Selectfluor 1 (1) or Accufluor 1 (2). It has been further demonstrated that it is possible to use these conditions to rapidly fluorinate quite complex molecules and isolate novel products in useful quantities.…”

“…Fluorination of electron rich aromatic systems with electrophilic fluorination reagents such as Selectfluor 1 (1) [1] and Accufluor 1 (2) [2] is an established process which has been well studied and is the subject of several useful and informative reviews [3][4][5] (Fig. 1).…”

Regio- and stereoselective synthesis of vicinal fluorohydrins

“…]octane bis(tetrafluoroborate) (NFTh) with water and styrene in acetonitrile gave 2-fluoro-1-phenylethanol regioselectively in 90% yield. Substituted styrenes reacted similarly (Scheme 77) [171]. Aryl-alkyl substituted tertiary alcohols can efficiently converted directly to vicinal fluorohydrins in high yield by reaction with Selectfluor TM F-Teda BF 4 in acetonitrile.…”