PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.
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.
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Natalia
N
Chernyak
Alexander S
AS
Dudnik
Chunhui
C
Huang
Vladimir
V
Gevorgyan
D002244:Carbon / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D011725:Pyridines; D012821:Silanes; D002244:Carbon; D006859:Hydrogen; C023666:pyridine; D012825:Silicon