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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
RÉSUMÉ

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.

MATÉRIAUX
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Marque
Description du produit

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