Gini, Andrea and Mancheno, Olga Garcia (2016) Mild Radical Oxidative sp(3)-Carbon-Hydrogen Functionalization: Innovative Construction of Isoxazoline and Dibenz[b,f]oxepine/azepine Derivatives. SYNLETT, 27 (4). pp. 526-539. ISSN 0936-5214, 1437-2096
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Direct carbon-hydrogen bond functionalization has emerged as a powerful synthetic method for the straightforward and modular functionalization of organic molecules. In this account, we described our latest contributions in the area of oxidative sp(3)-carbon-hydrogen bond functionalization using mild radical oxidants for the construction of structurally important heterocycles. We have developed two new methodologies in which a new class of substrate and an uncommon nucleophilic reagent have been introduced to the existing palette of reaction partners for oxidative carbon-hydrogen functionalization. To achieve these results, the 2,2,6,6-tetramethylpiperidinyloxyl (TEMPO) radical and a benzoyl peroxide/copper(I) system have been employed as oxidants for the dehydrogenative one-pot synthesis of N-alkoxycarbonyl-protected isoxazolines from hydroxylamines and for the synthesis of dibenz[b,f]oxepines, dibenzo[b,f]thiepines, and dibenz[b,f]azepines from simple xanthenes, thioxanthenes, and acridanes, respectively. 1 Introduction 2 2,2,6,6-Tetramethylpiperidinyloxyl-Mediated Dehydrogenative Formation and Trapping of Unstable Nitrones: Synthesis of N-Alkoxycarbonyl-Protected Isoxazoline Derivatives 3 Oxidative sp(3)-Carbon-Hydrogen Bond Functionalization and Ring Expansion with Trimethylsilyldiazomethane: Synthesis of Dibenzoxepines, Dibenzothiepines, and Dibenzazepines 4 Conclusions and Outlook
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-H BONDS; COPPER-CATALYZED REACTIONS; COUPLING REACTIONS; ORGANIC-SYNTHESIS; CONVENIENT REAGENT; CROSS-COUPLINGS; DIAZO-COMPOUNDS; C(SP(3))-H FUNCTIONALIZATION; 3+2 CYCLOADDITIONS; NITROXYL RADICALS; carbon-hydrogen functionalization; oxidations; radicals; peroxides; heterocycles |
| 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: | 11 Mar 2019 14:13 |
| Last Modified: | 11 Mar 2019 14:13 |
| URI: | https://pred.uni-regensburg.de/id/eprint/2361 |
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