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- W2773833148 abstract "The aim of this thesis was the development of transition metal-free radical aromatic substitutions mediated by weak, inexpensive, and non-toxic inorganic bases.In the beginning, the general preparation and properties of arenediazonium salts were given. An overview of existing reaction types of arenediazonium compounds from the old ones to the most modern was given. The major focus laid on the transformations of arenediazonium salts in the presence of weak bases. The key mechanistic steps were highlighted, where authors could propose a mechanism.Chapters 3 and 4 dealt with the generation of aryl radicals from arenediazonium tetrafluoroborates by very weak bases. This strategy was applied to the preparation of aromatic sulfides, selenides, tellurides, as well as diverse tert-butyl, alkyl, and i-propyl benzoates. Unexpected heterocyclic products were synthesized from arenediazonium salts using this method. In order to prove the proposed mechanisms, mechanistic investigations were made, involving spectroscopic and computational techniques and deuterium labeling. The postulated mechanisms involved homolysis of the initially formed diazoacetate or diazoformate. Mechanistic studies in thiolation reactions indicated the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals. In the alkoxycarbonylation reactions the aryl radical reacted with carbon monoxide to provide the acyl radical, which was confirmed by trapping experiments.Chapter 5 aimed to compare photoredox catalysis and base mediation in a radical aromatic trifluoromethylthiolation reaction. Three related synthetic protocols (two photocatalytic and one base-mediated) utilizing arenediazonium tetrafluoroborates as starting compounds were developed. Diverse aromatic trifluoromethyl sulfides were synthesized employing a photo-catalyzed protocol which afforded significantly higher yields." @default.
- W2773833148 created "2017-12-22" @default.
- W2773833148 creator A5001533325 @default.
- W2773833148 date "2017-11-23" @default.
- W2773833148 modified "2023-09-24" @default.
- W2773833148 title "Radical Aromatic Substitutions Mediated by Weak Bases" @default.
- W2773833148 hasPublicationYear "2017" @default.
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