PyDipSi: A general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes

Natalia Chernyak; Alexander S. Dudnik; Chunhui Huang; Vladimir Gevorgyan

doi:10.1021/ja1033167

PyDipSi: A general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes

Natalia Chernyak, Alexander S. Dudnik, Chunhui Huang, Vladimir Gevorgyan

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

173 Scopus citations

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.

Original language	English (US)
Pages (from-to)	8270-8272
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	132
Issue number	24
DOIs	https://doi.org/10.1021/ja1033167
State	Published - Jun 23 2010
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "PyDipSi: A general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes",

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.",

author = "Natalia Chernyak and Dudnik, {Alexander S.} and Chunhui Huang and Vladimir Gevorgyan",

year = "2010",

month = jun,

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AU - Dudnik, Alexander S.

AU - Huang, Chunhui

AU - Gevorgyan, Vladimir

PY - 2010/6/23

Y1 - 2010/6/23

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AB - 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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PyDipSi: A general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes

Abstract

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