Journal
ORGANIC LETTERS
Volume 17, Issue 9, Pages 2078-2081Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00602
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Funding
- National Natural Science Foundation of China [2009CB623505, 21403219]
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The oxidation of benzylpyridines forming benzoylpyridines was achieved based on a synergistic H4NI-AcOH catalyst and molecular oxygen in high yield under solvent-free conditions. This is the first nonmetallic catalytic system for this oxidation transformation using molecular oxygen as the oxidant. The catalytic system has a wide scope of substrates and excellent chemoselectivity, and this procedure can also be scaled up. The study of a preliminary reaction mechanism demonstrated that the oxidation of the C-sp(3)-H bonds of benzylpyridines was promoted by the pyridinium salts formed by AcOH and benzylpyridines. The synergistic effect of H4NI-AcOH was also demonstrated by control experiments.
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