Earth-Abundant Metal Catalysis Enabled by Counterion Activation
A precatalyst activation strategy has been developed for earth-abundant metal catalysis enabled by counterion dissociation and demonstrated through alkene hydroboration. Commercially available iron and cobalt tetrafluoroborate salts were found to catalyze
Agahi, Riaz,Challinor, Amy J.,Carter, Neil B.,Thomas, Stephen P.
supporting information
p. 993 - 997
(2019/02/14)
Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides
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.
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.
supporting information
p. 3373 - 3377
(2015/06/02)
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Liquid bromine as an electrophilic medium gives rise to skeletal rearrangements in a series of substrates: The Beckmann rearrangement of methyl 1-adamantyl ketone oxime to 1-acetamidoadamantane; the pinacone-pinacoline rearrangement; the cyclization of me
Baklan, V. F.,Antipenkova, L. S.,Zakharchenko, L. I.,Fesenko, T. E.,Kukhar, V. P.
p. 1102 - 1105
(2007/10/02)
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