Brandhofer, Tobias and Oezdemir, Ayseguel and Gini, Andrea and Mancheno, Olga Garcia (2019) Double Cu-Catalyzed Direct Csp(3)-H Azidation/CuAAC Reaction: A Direct Approach towards Demanding Triazole Conjugates. CHEMISTRY-A EUROPEAN JOURNAL, 25 (16). pp. 4077-4086. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
The first one-pot procedure for the double copper(I)-catalyzed oxidative Csp(3)-H azidation-CuAAC process, implying unstable azide intermediates and easy-to-remove reagents under water-tolerant conditions, is presented. The combination of tert-butyl hydroperoxide as oxidant and TMSN3 as azide source for the C-H bond azidation, which produces harmless side-products such as tBuOH and H2O, probed to be perfectly compatible with the following cycloaddition step. Highly demanding 1,2,3-triazoles could be then directly obtained in good overall yields by extraction or simple crystallization, thus avoiding chromatography purifications. The potential of this methodology, has also being highlighted by the successful reaction of alkynes presenting interesting complex biological moieties based for example on biotin, DNA base or cinchona alkaloid units.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; BOND OXIDATIVE FUNCTIONALIZATION; HYPERVALENT IODINE REAGENTS; CLICK-CHEMISTRY ROUTE; COUPLING REACTIONS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; BIOLOGICAL EVALUATION; RAPID SYNTHESIS; DIAZO TRANSFER; azidation; click chemistry; copper catalysis; oxidative C-H functionalization; triazoles |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Olga Garcia Mancheño |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Apr 2020 09:04 |
| Last Modified: | 20 Apr 2020 09:04 |
| URI: | https://pred.uni-regensburg.de/id/eprint/27358 |
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