- Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System
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The direct sulfonamidation of primary and secondary benzylic alcohols catalyzed by a 2,3,4,5-tetrafluorophenylboronic acid/oxalic acid co-catalytic system was examined. The reaction proceeds under mild conditions with readily available starting materials and has been shown to be gram-scalable without significant decrease of yield. Both primary and secondary benzylic alcohols were evaluated and afforded the desired sulfonamide products with good to excellent yields.
- Verdelet, Tristan,Ward, Robert M.,Hall, Dennis G.
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supporting information
p. 5729 - 5738
(2017/10/06)
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- Polyfluoroorganoboron-oxygen compounds. 1: Polyfluorinated aryl(dihydroxy)boranes and tri(aryl)boroxins
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A general preparative procedure for polyfluorinated aryl(dihydroxy)boranes C6H5-nFnB(OH)2 (n = 3 - 5) is described. Polyfluorinated aryl(dihydroxy)boranes are easily dehydrated to the corresponding tri(aryl)boroxins (C6H5-nFnBO)3 by thermal or chemical treatment. The property of the acids C6H5-nFnB(OH)2 to condensate depends on the number and on the position of the fluorine atoms in the aryl group. Examples of both classes of boron compounds were isolated as pure individuals and characterized by multinuclear NMR spectroscopy.
- Frohn,Adonin,Bardin,Starichenko
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p. 2827 - 2833
(2008/10/08)
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- (Fluoroorgano)fluoroboranes and -fluoroborates I: Synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes
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A convenient preparation of K[ArBF3] (Ar=2-C6H4F, 3-C6H4F, 4-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, 2,3,4,5-C6HF4 and C6F5) is offered and the IR and multinuclear NMR spectra of these salts are reported. Treatment of the trifluoroborate salts with BF3 in chlorocarbon solvents provides an easy synthetic route to the corresponding aryldifluoroboranes ArBF2. The multinuclear NMR spectra of ArBF2 are presented. The electron substituent effect of the [-BF3]--group shows this substituent as one of the strongest σ-electron donors, while its π-electron influence is negligible (σI=-0.32, σR=-0.07).
- Frohn,Franke,Fritzen,Bardin
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p. 127 - 135
(2007/10/03)
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