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PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.
J Am Chem Soc. 2010 Jun 23; 132(24):8270-2.JA

Abstract

A new general and easily installable silicon-tethered pyridyl-containing directing group (PyDipSi) that allows for highly efficient and regioselective Pd-catalyzed ortho C-H acyloxylation of arenes has been developed. It has also been demonstrated that this directing group can efficiently be removed as well as converted into a variety of other valuable functional groups. In addition, the installation of the PyDipSi directing group along with pivaloxylation and quantitative conversion of the PyDipSi group into a halogen functionality represents a formal three-step ortho oxygenation of haloarenes.

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Authors+Show Affiliations

Chernyak N
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Dudnik AS
No affiliation info available
Huang C
No affiliation info available
Gevorgyan V
No affiliation info available

MeSH

CarbonHydrocarbons, AromaticHydrogenPyridinesSilanesSilicon

Pub Type(s)

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

Language

eng

PubMed ID

20509671

Citation

Chernyak, Natalia, et al. "PyDipSi: a General and Easily Modifiable/traceless Si-tethered Directing Group for C-H Acyloxylation of Arenes." Journal of the American Chemical Society, vol. 132, no. 24, 2010, pp. 8270-2.
Chernyak N, Dudnik AS, Huang C, et al. PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes. J Am Chem Soc. 2010;132(24):8270-2.
Chernyak, N., Dudnik, A. S., Huang, C., & Gevorgyan, V. (2010). PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes. Journal of the American Chemical Society, 132(24), 8270-2. https://doi.org/10.1021/ja1033167
Chernyak N, et al. PyDipSi: a General and Easily Modifiable/traceless Si-tethered Directing Group for C-H Acyloxylation of Arenes. J Am Chem Soc. 2010 Jun 23;132(24):8270-2. PubMed PMID: 20509671.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes. AU - Chernyak,Natalia, AU - Dudnik,Alexander S, AU - Huang,Chunhui, AU - Gevorgyan,Vladimir, PY - 2010/6/1/entrez PY - 2010/6/1/pubmed PY - 2010/9/16/medline SP - 8270 EP - 2 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 24 N2 - A new general and easily installable silicon-tethered pyridyl-containing directing group (PyDipSi) that allows for highly efficient and regioselective Pd-catalyzed ortho C-H acyloxylation of arenes has been developed. It has also been demonstrated that this directing group can efficiently be removed as well as converted into a variety of other valuable functional groups. In addition, the installation of the PyDipSi directing group along with pivaloxylation and quantitative conversion of the PyDipSi group into a halogen functionality represents a formal three-step ortho oxygenation of haloarenes. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20509671/PyDipSi:_a_general_and_easily_modifiable/traceless_Si_tethered_directing_group_for_C_H_acyloxylation_of_arenes_ L2 - https://doi.org/10.1021/ja1033167 DB - PRIME DP - Unbound Medicine ER -