Studies on Organophosphorus Catalyzed C(SP³)–H Amination for the Synthesis of Benzimidazoles
Name
pombar-gpombar-sm-chemistry-2022-thesis.pdf
Description
Thesis PDF
Size
7.75 MB
Format
Adobe PDF
Checksum (MD5)
046a4da406dfcb67d54cfd24f71ab639
Author(s)
Pombar, Gisselle
Advisor(s)
Radosevich, Alexander T.
Date Issued
September 2022
Publisher
Massachusetts Institute of Technology
Abstract
A PIII/PV=O-catalyzed C(sp³)–H amination has been realized for (dihydro)benzimidazole synthesis. This work reports: (1) optimization of organophosphorus-catalyzed C(sp³)–H functionalization; (2) scope studies to benzimidazoles by in situ oxidation of the corresponding dihydrobenzimidazole; and (3) insight into the reaction mechanism through in situ spectroscopic monitoring under catalytic conditions and Hammett linear free energy relationship studies. The synthetic method and mechanistic information provide insight into design principles for the expansion of C(sp³)–H functionalization reactions through PIII/PV=O O-atom transfer reactivity.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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