- Organocatalytic Aerobic Oxidation of α-Fluoroalkyl Alcohols to Fluoroalkyl Ketones at Room Temperature
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The organocatalytic aerobic oxidation of electron-deficient α-fluoroalkyl alcohols at room temperature is described. The resulting fluoroalkyl ketones are versatile synthetic intermediates for a variety of fluorine-containing molecules. This otherwise difficult transformation has now been accomplished by the reaction of α-fluoroalkyl alcohols with N-oxyl radicals, catalytically generated from 9-azabicyclo[3.3.1]nonan-3-one N-oxyl/nitrogen oxide (keto-ABNO/NOx) and oxygen in acetic acid (AcOH), affording the corresponding fluoroalkyl ketones in high yield. This operationally simple reaction can be performed under mild conditions, and was applied to a wide range of alcohols (20 examples), thus demonstrating a high functional group tolerance. Moreover, a modified one-pot protocol based on this method was able to convert an aldehyde to a trifluoromethyl ketone on a gram scale.
- Kadoh, Yoichi,Tashiro, Masayuki,Oisaki, Kounosuke,Kanai, Motomu
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p. 2193 - 2198
(2015/07/27)
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- Oxime derivatives and the use thereof as latent acids
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Compounds of formula I, II and III, wherein wherein R1is for example hydrogen, C1-C12alkyl, C3-C30cycloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, phenyl, whic
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- Remarkably effective and simple syntheses of enantiomerically pure secondary carbinols from achiral ketones
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The chiral oxazaborolidine (1)-catalyzed reduction of the ketones 2, 6 and 8 has provided simple access to the chiral secondary carbinols 3, 7, and 9 in very high enantiomeric purity.
- Corey,Cheng,Cimprich,Sarshar
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p. 6835 - 6838
(2007/10/02)
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