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Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers

Singh, B.K.; Jana, R.

Journal of Organic Chemistry 81(3): 831-841

2016

ISSN/ISBN: 1520-6904
PMID: 26762789
DOI: 10.1021/acs.joc.5b02302
Accession: 058217037
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We report here a practical method for the ortho C-H hydroxylation of benzamides with inexpensive copper(II) acetate monohydrate and a pyridine ligand. An intra- and intermolecular ligand combination was explored to achieve regio- and chemoselective hydroxylation. Interestingly, typical regiochemical scrambling associated with the C-H activation was further resolved by introducing a ligand-directed ortho hydroxylation of haloarenes and aryl methyl ethers.

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