Oxidative transformation of azides to aryl nitriles using DIB/TBHP: scope and mechanistic insights

Bis(tert-butylperoxy)iodobenzene, generated in situ by the reaction between diacetoxyl iodobenzene (DIB) and tert-butyl hydroperoxide (TBHP), was used in the oxidative transformation of primary azides to nitriles, and secondary azides to ketones.

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Bibliographic Details
Published inTetrahedron letters Vol. 53; no. 35; pp. 4766 - 4769
Main Authors Zhao, Yi, Chew, Xinying, Leung, Gulice Y.C., Yeung, Ying-Yeung
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.08.2012
Elsevier
Subjects
Aromatic compounds
Chemistry
Chemistry, Organic
Hypervalent iodine
Ketones
Mechanism
Nitrile
Nitriles
Oxidation
Physical Sciences
Science & Technology
Selectivity
Tetrahedrons
Transformations
Oxidation
Selectivity
Nitrile
Hypervalent iodine
Mechanism
HALIDES
COMPLEXES
BROMIDES
HIGHLY EFFICIENT
MEDIATED CYANATION
DEHYDRATION
PRIMARY AMIDES
GENERATION
PALLADIUM-CATALYZED CYANATION
ALDOXIMES
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Summary:Bis(tert-butylperoxy)iodobenzene, generated in situ by the reaction between diacetoxyl iodobenzene (DIB) and tert-butyl hydroperoxide (TBHP), was used in the oxidative transformation of primary azides to nitriles, and secondary azides to ketones.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.06.131