Studies on Organophosphorus Catalyzed C(SP³)–H Amination for the Synthesis of Benzimidazoles

dc.contributor.advisor	Radosevich, Alexander T.
dc.contributor.author	Pombar, Gisselle
dc.date.accessioned	2023-01-19T18:41:17Z
dc.date.available	2023-01-19T18:41:17Z
dc.date.issued	2022-09
dc.date.submitted	2022-10-25T17:27:57.210Z
dc.identifier.uri	https://hdl.handle.net/1721.1/147263
dc.description.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.
dc.publisher	Massachusetts Institute of Technology
dc.rights	In Copyright - Educational Use Permitted
dc.rights	Copyright MIT
dc.rights.uri	http://rightsstatements.org/page/InC-EDU/1.0/
dc.title	Studies on Organophosphorus Catalyzed C(SP³)–H Amination for the Synthesis of Benzimidazoles
dc.type	Thesis
dc.description.degree	S.M.
dc.contributor.department	Massachusetts Institute of Technology. Department of Chemistry
mit.thesis.degree	Master
thesis.degree.name	Master of Science in Chemistry