A divergent and selective synthesis of ortho- and para-quinones from phenols

作者：Huang Zheng; Kwon Ohhyeon; Esguerra Kenneth Virgel N; Lumb Jean Philip^*

来源：Tetrahedron, 2015, 71(35): 5871-5885.

DOI：10.1016/j.tet.2015.04.095

• Phenol
• C-H oxidation
• Quinone
• Aerobic catalysis
• Copper
• Estrone

We describe a divergent synthesis of substituted ortho- and para-quinones by catalytic aerobic oxygenation of phenols. Substituted quinones are omnipresent in chemistry and biology, but their synthesis frequently suffers from low efficiency and poor scope. Our methodology employs a catalytic aerobic di-functionalization of phenols to aryloxy-ortho-quinones. Regioselective substitution with an alcohol provides the alkoxy substituted ortho- or para-quinone, while hydrolysis affords the para-hydroxyquinone. These are mild and selective conditions for the synthesis of diversely substituted quinones from readily available phenol starting materials.

• 出版日期2015-9-2
• 单位McGill