90416-80-1Relevant academic research and scientific papers
Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Figuccia, Aude L.A.,Fletcher, Ai M.,Heijnen, Dorus,Lee, James A.,Morris, Melloney J.,Kennett, Alice M.R.,Roberts, Paul M.,Thomson, James E.
, p. 3373 - 3377 (2015/06/02)
The incorporation of alkoxy ligands within a range of alkoxyfluoroboranes and dialkoxyfluoroboranes results in fluoroborane reagents with attenuated Lewis acidity and increased ability to donate fluoride ion(s) when compared to boron trifluoride itself. Pinacolatoboron fluoride (pinBF), prepared in situ from BF3·OEt2 and bis(O-trimethylsilyl)pinacol, has been identified as an efficient fluoride donor which allows highly stereoselective SN1-type epoxide ring-opening (with retention of configuration) of a range of trans-β-methyl-substituted aryl epoxides to give the corresponding syn-fluorohydrins. The substrate scope of this transformation is more broad than the analogous protocol using boron trifluoride alone.
β-fluoroamphetamines via the stereoselective synthesis of benzylic fluorides
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.,Tyte, Melloney J.
supporting information; experimental part, p. 2936 - 2939 (2010/09/10)
A range of substituted aryl epoxides undergo efficient ring-opening hydrofluorination upon treatment with 0.33 equiv of BF3-OEt 2 in CH2Cl2 at -20 -°C to give the corresponding syn-fluorohydrins, consistent with a mechanism involving a stereoselective SN1-type epoxide ring-opening process. The benzylic fluoride products of these reactions are valuable templates for further elaboration, as demonstrated by the preparation of a range of aryl-substituted β-fluoroamphetamines.
Potassium dihydrogen trifluoride: a novel fluorinating reagent for ring-opening of epoxides
Tamura, Masanori,Shibakami, Motonari,Arimura, Takashi,Kurosawa, Shigeru,Sekiya, Akira
, p. 1 - 4 (2007/10/02)
It has been found that potassium dihydrogen trifluoride is an efficient and easy-to-handle solid reagent for the ring-opening reaction of epoxides giving fluorhydrins regio- and stereo-selectively.The reaction proceeds via cis-addition of HF to the epoxide. - Keywords: Potassium dihydrogen trifluoride; Fluorinating reagent; Ring-opening; Epoxides; Fluorohydrin synthesis
HIGHLY SELECTIVE RING OPENING OF EPOXIDES WITH SILICON TETRAFLUORIDE: PREPARATION OF FLUOROHYDRINS
Shimizu, Makoto,Yoshioka, Hirosuke
, p. 4101 - 4104 (2007/10/02)
Regio-, stereo-, and chemoselective transformation of epoxides into fluorohydrins with silicone tetrafluoride is described.
