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Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.
J Am Chem Soc. 2012 Mar 28; 134(12):5528-31.JA

Abstract

The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction.

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Authors+Show Affiliations

Gulevich AV
Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607-7061, United States.
Melkonyan FS
No affiliation info available
Sarkar D
No affiliation info available
Gevorgyan V
No affiliation info available

MeSH

CatalysisHydrocarbons, AromaticOxygenPalladiumResorcinolsSilicon Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

22414133

Citation

Gulevich, Anton V., et al. "Double-fold C-H Oxygenation of Arenes Using PyrDipSi: a General and Efficient Traceless/modifiable Silicon-tethered Directing Group." Journal of the American Chemical Society, vol. 134, no. 12, 2012, pp. 5528-31.
Gulevich AV, Melkonyan FS, Sarkar D, et al. Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group. J Am Chem Soc. 2012;134(12):5528-31.
Gulevich, A. V., Melkonyan, F. S., Sarkar, D., & Gevorgyan, V. (2012). Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group. Journal of the American Chemical Society, 134(12), 5528-31. https://doi.org/10.1021/ja3010545
Gulevich AV, et al. Double-fold C-H Oxygenation of Arenes Using PyrDipSi: a General and Efficient Traceless/modifiable Silicon-tethered Directing Group. J Am Chem Soc. 2012 Mar 28;134(12):5528-31. PubMed PMID: 22414133.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group. AU - Gulevich,Anton V, AU - Melkonyan,Ferdinand S, AU - Sarkar,Dhruba, AU - Gevorgyan,Vladimir, Y1 - 2012/03/19/ PY - 2012/3/15/entrez PY - 2012/3/15/pubmed PY - 2012/7/28/medline SP - 5528 EP - 31 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 134 IS - 12 N2 - The efficient Pd-catalyzed double-fold C-H oxygenation of arenes into resorcinols using the newly developed 2-pyrimidyldiisopropylsilyl (PyrDipSi) directing group is described. Its use allows for the sequential introduction of OAc and OPiv groups in a one-pot manner to produce orthogonally protected resorcinol derivatives. The PyrDipSi group is superior to the previously developed 2-pyridyldiisopropylsilyl (PyDipSi) group, as it is efficient for monooxygenation of ortho-substituted arenes. Notably, the PyrDipSi group can be easily installed into arene molecules and can be easily removed or modified after the oxygenation reaction. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22414133/Double_fold_C_H_oxygenation_of_arenes_using_PyrDipSi:_a_general_and_efficient_traceless/modifiable_silicon_tethered_directing_group_ L2 - https://doi.org/10.1021/ja3010545 DB - PRIME DP - Unbound Medicine ER -