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Literature DB >> 19449353

C-H hydroxylation using a heterocyclic catalyst and aqueous H2O2.

Nichole D Litvinas¹, Benjamin H Brodsky, J Du Bois.

Abstract

Substituted benzoxathiazines function as catalysts for the selective hydroxylation of tertiary C-H bonds. Mechanistic studies have revealed an unanticipated disparity between oxaziridine reactivity and catalyst performance and have given way to a new catalyst and an aqueous H(2)O(2) reaction protocol that greatly facilitate such transformations (see scheme).

Entities: Chemical

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Year: 2009 PMID： 19449353 DOI： 10.1002/anie.200901353

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

20 in total

1. Metal-coordinated water-soluble cavitands act as C-H oxidation catalysts.

Authors: Katherine E Djernes; Orly Moshe; Magi Mettry; Donald D Richards; Richard J Hooley
Journal: Org Lett Date: 2012-01-24 Impact factor: 6.005

2. Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.

Authors: Shea L Johnson; Michael K Hilinski
Journal: J Org Chem Date: 2019-06-19 Impact factor: 4.354

10. Site-selective, catalytic, and diastereoselective sp³ C-H hydroxylation and alkoxylation of vicinally functionalized lactams.

Authors: Timothy K Beng; Victoria Shearer; Rachel Davey; Ivianne Redman
Journal: RSC Adv Date: 2020-05-27 Impact factor: 4.036

C-H hydroxylation using a heterocyclic catalyst and aqueous H2O2.

1. Metal-coordinated water-soluble cavitands act as C-H oxidation catalysts.

2. Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight.

3. Efficient stereo- and regioselective hydroxylation of alkanes catalysed by a bulky polyoxometalate.

4. Rhodium-Catalyzed C-H Amination - An Enabling Method for Chemical Synthesis.

5. Dictating Thermodynamic Control through Tethering: Applications to Stereoselective Bis-Spiroketal Synthesis.

6. Metal-catalyzed nitrogen-atom transfer methods for the oxidation of aliphatic C-H bonds.

7. Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.

8. A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.

9. Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol.

10. Site-selective, catalytic, and diastereoselective sp³ C-H hydroxylation and alkoxylation of vicinally functionalized lactams.