Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor

We present protocols for the oxidation of alcohols and aldehydes and for the oxidative cyclization of diols which use a combination of Selectfluor and NaBr. For most substrates, the optimal solvent system is a 1:1 mixture of CH3CN/H2O, but, in select cases, biphasic 1:1 mixtures of EtOAc/H2O or CH2C...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 15; pp. 11240 - 11252
Main Authors Joshi, Harshit, Paul, Debobrata, Sathyamoorthi, Shyam
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.08.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
SELECTIVE OXIDATION
BROMINATION
LACTONES
KINETIC RESOLUTION
BONDS
LACTONIZATION
FLUORINATION
EFFICIENT
CYCLIZATION
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Summary:We present protocols for the oxidation of alcohols and aldehydes and for the oxidative cyclization of diols which use a combination of Selectfluor and NaBr. For most substrates, the optimal solvent system is a 1:1 mixture of CH3CN/H2O, but, in select cases, biphasic 1:1 mixtures of EtOAc/H2O or CH2Cl2/H2O are superior. This procedure is operationally simple, uses inexpensive and readily available reagents, and tolerates a variety of functional groups. Mechanistic studies suggest that the active oxidant is hypobromous acid, generated by the almost instantaneous oxidation of Br– by Selectfluor in an aqueous milieu.
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content type line 23
equal contribution
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01307