Journal
ACS CATALYSIS
Volume 6, Issue 10, Pages 6520-6524Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02237
Keywords
C-H amination; O-phenyl carbamates; benzoxazolone; chemoselective; nitrene insertion
Categories
Funding
- DST INSPIRE fund [GAP0548]
- CSIR fund [CSC0301]
- DST (Department of Science and Technology)
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Rhodium(II) can effectively promote the activation and cyclization of arylcarbamate substrates to yield benzoxazolones via an intramolecular nitrene C-H insertion reaction. Investigation of the substrate scope shows that the reaction undergoes selective aromatic C(sp(2))-H amination over more labile o-C(sp(3))-H bonds. Observation of inverse secondary KIE (P-H/P-D = 0.42 +/- 0.03) indicates involvement of aromatic electrophilic substitution mechanism for this aryl C-H amidation transformation.
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