Iron-Catalyzed Arene C–H Amidation Using Functionalized Hydroxyl Amines at Room Temperature

Iron-Catalyzed Arene C–H Amidation Using Functionalized Hydroxyl Amines at Room Temperature

Herein, we report Fe(III)(TPP)Cl as an effective catalyst for promoting arene C–H amidation through intramolecular cyclization of N-tosyloxyarylcarbamate substrates. The reaction proceeds via nitrene (outer sphere pathway) C­(sp2)–H insertion to yield benzoxazolones under external-oxidant-free condi...

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Veröffentlicht in:ACS catalysis 2018-09, Vol.8 (9), p.8369-8375
Hauptverfasser: Prasanthi, A. V. G, Begum, Samiyara, Srivastava, Hemant Kumar, Tiwari, Sandip Kumar, Singh, Ritesh
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container_end_page 8375
container_issue 9
container_start_page 8369
container_title ACS catalysis
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creator Prasanthi, A. V. G
Begum, Samiyara
Srivastava, Hemant Kumar
Tiwari, Sandip Kumar
Singh, Ritesh
description Herein, we report Fe(III)(TPP)Cl as an effective catalyst for promoting arene C–H amidation through intramolecular cyclization of N-tosyloxyarylcarbamate substrates. The reaction proceeds via nitrene (outer sphere pathway) C­(sp2)–H insertion to yield benzoxazolones under external-oxidant-free conditions at ambient temperature. The method is operationally simple and scalable with high-functional-group tolerance. Preliminary experimental and computational data indicates involvement of electrophilic aromatic substitution mechanism for this aryl C–H amidation transformation, distinct from operating mechanism reported previously in aryl C–H amination using azide-based substrates.
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