Journal
ORGANIC LETTERS
Volume 19, Issue 20, Pages 5593-5596Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02731
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Funding
- National Natural Science Foundation of China [21672196, 21404096, 21602001, U1463202]
- Anhui Provincial Natural Science Foundation [1608085M1324]
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In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.
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