Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 1, Pages 184-191Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901356
Keywords
homogeneous catalysis; hypervalent iodine; N-heterocycles; organocatalysis; oxidative transformations
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Funding
- Fonds der Chemischen Industrie
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The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the alpha-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the alpha-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements.
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