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J Am Chem Soc. 2010 Jun 23;132(24):8270-2. doi: 10.1021/ja1033167.

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

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  • 1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.


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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