Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides

Alexander J. Cresswell; Stephen G. Davies; Aude L. A. Figuccia; Ai M. Fletcher; Dorus Heijnen; James A. Lee; Melloney J. Morris; Alice M. R. Kennett; Paul M. Roberts; James E. Thomson

doi:10.1016/j.tetlet.2014.12.044

Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides

Alexander J. Cresswell, Stephen G. Davies, Aude L. A. Figuccia, Ai M. Fletcher, Dorus Heijnen, James A. Lee, Melloney J. Morris, Alice M. R. Kennett, Paul M. Roberts, James E. Thomson

Research output: Contribution to journal › Article › peer-review

12 Citations (SciVal)

Abstract

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 S_N1-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.

Original language	English
Pages (from-to)	3373-3377
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.044
Publication status	Published - 3 Jun 2015

Keywords

Benzylic fluoride
Epoxide
Nucleophilic fluorination

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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10.1016/j.tetlet.2014.12.044

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Cresswell, A. J., Davies, S. G., Figuccia, A. L. A., Fletcher, A. M., Heijnen, D., Lee, J. A., Morris, M. J., Kennett, A. M. R., Roberts, P. M., & Thomson, J. E. (2015). Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides. Tetrahedron Letters, 56(23), 3373-3377. https://doi.org/10.1016/j.tetlet.2014.12.044

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title = "Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides",

abstract = "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.",

keywords = "Benzylic fluoride, Epoxide, Nucleophilic fluorination",

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doi = "10.1016/j.tetlet.2014.12.044",

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T1 - Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides

AU - Cresswell, Alexander J.

AU - Davies, Stephen G.

AU - Figuccia, Aude L. A.

AU - Fletcher, Ai M.

AU - Heijnen, Dorus

AU - Lee, James A.

AU - Morris, Melloney J.

AU - Kennett, Alice M. R.

AU - Roberts, Paul M.

AU - Thomson, James E.

PY - 2015/6/3

Y1 - 2015/6/3

N2 - 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.

AB - 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.

KW - Benzylic fluoride

KW - Epoxide

KW - Nucleophilic fluorination

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DO - 10.1016/j.tetlet.2014.12.044

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides

Abstract

Keywords

ASJC Scopus subject areas

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