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  • Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.

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 (2012-03-15)
Anton V Gulevich, Ferdinand S Melkonyan, Dhruba Sarkar, Vladimir Gevorgyan
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Resorcinol, ≥98%, FG
Sigma-Aldrich
Resorcinol, ReagentPlus®, 99%
Sigma-Aldrich
Resorcinol, meets analytical specification of Ph. Eur., BP, 98.5-100.5% (calc. to the dried substance)
Sigma-Aldrich
Resorcinol, ACS reagent, ≥99.0%
Supelco
Resorcinol, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
Resorcinol, BioXtra, ≥99%
Sigma-Aldrich
Resorcinol, JIS special grade, ≥99.0%
Sigma-Aldrich
Resorcinol, SAJ first grade, ≥98.0%