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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

379 Scopus citations

Abstract

(Chemical Equation Presented) 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 [D ₆]Ac₂O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).

Original language	English (US)
Pages (from-to)	7420-7424
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	45
DOIs	https://doi.org/10.1002/anie.200502767
State	Published - Dec 1 2005

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Access to Document

10.1002/anie.200502767

Cite this

Giri, R., Liang, J., Lei, J. G., Li, J. J., Wang, D. H., Chen, X., Naggar, I. C., Guo, C., Foxman, B. M., & Yu, J. Q. (2005). 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. Angewandte Chemie - International Edition, 44(45), 7420-7424. https://doi.org/10.1002/anie.200502767

@article{d6540439f1974739bc37a3a6be409495,

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",

abstract = "(Chemical Equation Presented) 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 [D 6]Ac2O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).",

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

year = "2005",

month = dec,

day = "1",

doi = "10.1002/anie.200502767",

language = "English (US)",

volume = "44",

pages = "7420--7424",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "45",

}

Giri, R, Liang, J, Lei, JG, Li, JJ, Wang, DH, Chen, X, Naggar, IC, Guo, C, Foxman, BM & Yu, JQ 2005, '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', Angewandte Chemie - International Edition, vol. 44, no. 45, pp. 7420-7424. https://doi.org/10.1002/anie.200502767

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. / Giri, Ramesh; Liang, Jue; Lei, Jian Guang et al.
In: Angewandte Chemie - International Edition, Vol. 44, No. 45, 01.12.2005, p. 7420-7424.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Pd-catalyzed stereoselective oxidation of methyl groups by inexpensive oxidants under mild conditions

T2 - A dual role for carboxylic anhydrides in catalytic C-H bond oxidation

AU - Giri, Ramesh

AU - Liang, Jue

AU - Lei, Jian Guang

AU - Li, Jiao Jie

AU - Wang, Dong Hui

AU - Chen, Xiao

AU - Naggar, Isaac Clement

AU - Guo, Chengyun

AU - Foxman, Bruce M.

AU - Yu, Jin Quan

PY - 2005/12/1

Y1 - 2005/12/1

N2 - (Chemical Equation Presented) 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 [D 6]Ac2O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).

AB - (Chemical Equation Presented) 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 [D 6]Ac2O as the solvent shows that the acetyl group incorporated into the product is from acetic anhydride rather than the oxidant (see scheme).

UR - http://www.scopus.com/inward/record.url?scp=28044468663&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=28044468663&partnerID=8YFLogxK

U2 - 10.1002/anie.200502767

DO - 10.1002/anie.200502767

M3 - Article

C2 - 16247822

AN - SCOPUS:28044468663

SN - 1433-7851

VL - 44

SP - 7420

EP - 7424

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 45

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this