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.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3371766 | PMC |
| http://dx.doi.org/10.1021/ja3010545 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Double-Fold Ortho and Remote C-H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL.
Org Lett
August 2019
Center of Bio-Medical Research, Division of Molecular Synthesis & Drug Discovery , SGPGIMS Campus, Raebareli Road , Lucknow 226014 , Uttar Pradesh , India.
A double-fold ortho and remote C-H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C-H activation processes, respectively. While Beg (eg = ethylene glycolate) directs the C-H activation at ortho positions, a combination of HBpin and Bpin activates remote C-H bonds.
View Article and Find Full Text PDFPd-Catalyzed C-H Alkylation of Arenes Using PyrDipSi, a Transformable and Removable Silicon-Tethered Directing Group.
Chemistry
August 2016
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor St, Rm 4500, Chicago, IL, 60607, USA.
An efficient Pd-catalyzed ortho-C-H alkylation reaction of arenes using a transformable and removable Si-tethered pyridyldiisopropylsilyl (PyrDipSi) directing group has been developed. In addition, the PyrDipSi directing group allows for an efficient sequential double-fold C-H alkylation/oxygenation of arenes to produce meta-alkylated phenols. This directing group can easily be removed or converted into valuable functionalities, such as aryl, iodo, boronic ester, or phenol.
View Article and Find Full Text PDFRuthenium-catalyzed double-fold C-H tertiary alkoxycarbonylation of arenes using di-tert-butyl dicarbonate.
Chem Commun (Camb)
November 2014
School of Materials Science and Engineering, Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China.
An efficient ruthenium-catalyzed double-fold C-H alkoxycarbonylation of arenes was developed using di-tert-butyl dicarbonate as the tertiary esterification reagent, which leads to a direct route to valuable 2,6-dicarboxylated products.
View Article and Find Full Text PDFFused heteroaromatic dihydrosiloles: synthesis and double-fold modification.
Org Lett
May 2013
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States.
An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity.
View Article and Find Full Text PDFDouble-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.
J Am Chem Soc
March 2012
Department of Chemistry, University of Illinois at Chicago, Chicago, Illinois 60607-7061, United States.
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.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!