Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 9, Pages 1820-1832Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00061b
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Funding
- SERB [EMR/2017/002827]
- CSIR, Government of India [02(0278)/16/EMR-II]
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A Pd-catalyzed aerobic approach to access C4-aryl benzoxazoles by tandem C-H ortho-arylation and acid-mediated annulation of 2-amidophenol has been presented. The directing potential of the -NHCOR group over the -OH group was exploited for selective arylation adjacent to the amide group. Deuterium labeling experiments suggest that palladation predominantly occurs adjacent to the -NHCOR group and is the key step during benzoxazole formation. One-pot hydrolysis of the resulting C4-arylated benzoxazole was also accomplished to access structurally challenging 3-aryl aminophenols for further applications.
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