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Mild and General Access to Diverse 1H-Benzotriazolesvia Diboron-Mediated N–OH Deoxygenation and Palladium-Catalyzed C–C andC–N Bond Formation
| Content Provider | PubMed Central |
|---|---|
| Author | Venkateshwarlu, Gurram Akula, Hari K. Ramesh, Garlapati Pottabathini, Narender Lakshman, Mahesh K. |
| Abstract | Benzotriazoles are a highly important class of compounds withbroad-ranging applications in such diverse areas as medicinal chemistry, asauxiliaries in organic synthesis, in metallurgical applications, in aircraftdeicing and brake fluids, and as antifog agents in photography. Although thereare numerous approaches to N-substituted benzotriazoles, the essentially onegeneral method to N-unsubstituted benzotriazoles is via diazotization ofo-phenylenediamines, which can be limited by theavailability of suitable precursors. Other methods to N-unsubstituedbenzotriazoles are quite specialized. Although reduction of1-hydroxy-1H-benzotriazoles is known the reactions are notparticularly convenient or broadly applicable. This presents a limitation foreasy access to and availability of diverse benzotriazoles. Herein, wedemonstrate a new, broadly applicable method to diverse1H-benzotriazoles via a mild diboron-reagent mediateddeoxygenation of 1-hydroxy-1H-benzotriazoles. We have alsoevaluated sequential deoxygenation and Pd-mediated C–C and C–Nbond formation as a one-pot process for further diversification of thebenzotriazole moiety. However, results indicated that purification of thedeoxygenation product prior to the Pd-mediated reaction is critical to thesuccess of such reactions. The overall chemistry allows for facile access to avariety of new benzotriazoles. Along with the several examples presented, adiscussion of the advantages of the approaches is described, as also a possiblemechanism for the deoxygenation process. |
| Related Links | http://dx.doi.org/10.1002/adsc.201400889 |
| Ending Page | 462 |
| Page Count | 12 |
| Starting Page | 451 |
| File Format | |
| ISSN | 16154150 |
| e-ISSN | 16154169 |
| Journal | Advanced synthesis & catalysis |
| Issue Number | 2-3 |
| Volume Number | 357 |
| Language | English |
| Publisher Date | 2015-02-09 |
| Access Restriction | Open |
| Subject Keyword | Organic Chemistry Catalysis Research in Higher Education |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
