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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Access to C4-arylated benzoxazoles from 2-amidophenol through C-H activation
Kanchanbala Sahoo1, Priyanka Pradhan1, Niranjan Panda1
1Department of Chemistry, National Institute of Technology Rourkela, Odisha 769008, India. npanda@nitrkl.ac.in.
Abstract:
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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