2026-09-19T13:29:54Zhttps://dspace.mit.edu/server/oai/requestoai:dspace.mit.edu:1721.1/1472632023-01-20T03:38:19Zcom_1721.1_7582com_1721.1_7581col_1721.1_131023
Radosevich, Alexander T.
Pombar, Gisselle
Massachusetts Institute of Technology. Department of Chemistry
2023-01-19T18:41:17Z
2023-01-19T18:41:17Z
2022-09
2022-10-25T17:27:57.210Z
https://hdl.handle.net/1721.1/147263
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.
S.M.
Massachusetts Institute of Technology
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Studies on Organophosphorus Catalyzed C(SP³)–H Amination for the Synthesis of Benzimidazoles
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Master
Master of Science in Chemistry
Publication
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<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.</Abstract>
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