Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation

Ramesh Giri; Jue Liang; Jian-Guang Lei; Jiao-Jie Li; Dong-Hui Wang; Xiao Chen; Isaac Clement Naggar; Chengyun Guo; Bruce M Foxman; Jin-Quan Yu

doi:10.1002/anie.200502767

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Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation

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Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation

Ramesh Giri, Jue Liang, Jian-Guang Lei, Jiao-Jie Li, Dong-Hui Wang, Xiao Chen, Isaac Clement Naggar, Chengyun Guo, Bruce M Foxman and Jin-Quan Yu

Angewandte Chemie (International ed.), Vol.44(45), pp.7420-7424

11/18/2005

DOI: https://doi.org/10.1002/anie.200502767

PMID: 16247822

Abstract

oxidation

CH activation

palladium

asymmetric catalysis

peroxides

Unactivated CH3 groups in 2-oxazolines are oxidized by inexpensive oxidants, such as tert-butyl peroxyacetate and lauroyl peroxide, in the presence of a catalytic amount of Pd(OAc)2. Carboxylic anhydrides are essential for both the oxidation of the PdC bonds and regeneration of Pd(OAc)2. The use of [D6]Ac2O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).

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Title: Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation
Creators: Ramesh Giri - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Jue Liang - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Jian-Guang Lei - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Jiao-Jie Li - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Dong-Hui Wang - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Xiao Chen - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Isaac Clement Naggar - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Chengyun Guo - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Bruce M Foxman - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Jin-Quan Yu - Department of Chemistry, Brandeis University, Waltham, MA 02454-9110, USA, Fax: (+1) 781-736-2516
Publication Details: Angewandte Chemie (International ed.), Vol.44(45), pp.7420-7424
Publisher: WILEY-VCH Verlag
Number of pages: 5
Identifiers: 9923989569101921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Pd-Catalyzed Stereoselective Oxidation of Methyl Groups by Inexpensive Oxidants under Mild Conditions: A Dual Role for Carboxylic Anhydrides in Catalytic CH Bond Oxidation

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