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Literature DB >> 25479376

Chemoselective hydroxylation of aliphatic sp3 C-H bonds using a ketone catalyst and aqueous H2O2.

Abstract

The first ketone-catalyzed method for the oxidation of aliphatic C-H bonds is reported. The reaction conditions employ aryl trifluoromethyl ketones in catalytic amounts and hydrogen peroxide as the terminal oxidant. Hydroxylation is stereospecific and chemoselective for tertiary over secondary C-H bonds. A catalytic cycle invoking a dioxirane as the active oxidant is proposed.

Entities: Chemical

Year: 2014 PMID： 25479376 DOI： 10.1021/ol503410e

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

6 in total

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

Authors: Pablo J Cabrera; Melissa Lee; Melanie S Sanford
Journal: J Am Chem Soc Date: 2018-04-13 Impact factor: 15.419

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

6. Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp³)-H amination catalyzed by an iminium salt.

Authors: Logan A Combee; Balaram Raya; Daoyong Wang; Michael K Hilinski
Journal: Chem Sci Date: 2017-11-27 Impact factor: 9.825

6 in total

Chemoselective hydroxylation of aliphatic sp3 C-H bonds using a ketone catalyst and aqueous H2O2.

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

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

3. Remote C(sp³)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.

4. Amine Organocatalysis of Remote, Chemoselective C(sp³)-H Hydroxylation.

5. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

6. Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp³)-H amination catalyzed by an iminium salt.

Chemoselective hydroxylation of aliphatic sp3 C-H bonds using a ketone catalyst and aqueous H2O2.

1. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

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

3. Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.

4. Amine Organocatalysis of Remote, Chemoselective C(sp3)-H Hydroxylation.

5. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

6. Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt.

3. Remote C(sp³)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate.

4. Amine Organocatalysis of Remote, Chemoselective C(sp³)-H Hydroxylation.

6. Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp³)-H amination catalyzed by an iminium salt.