5 years ago

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines

Iodine-Catalyzed Oxidative Coupling To Construct C–O Bonds for the Synthesis of 2,3-Dihydrooxepines
Yan-dong Wu, An-xin Wu, Xiao Geng, Xia Wu, Peng Zhao
The iodine-catalyzed catalytic formal [3 + 3 + 1] cycloaddition for the preparation of a seven-membered O-heterocyclic ring is presented, which is an achievement of methyl and carbonyl group reactivity of 3-methyl-5-pyrazolones to forge the Csp3–O bond. This novel protocol provides a straightforward and efficient access to structurally diverse fused O-heterocycles through an iodine-catalyzed iodination/Kornblum oxidation/oxidative coupling/C–O bond formation cascade reaction. This approach demonstrates the unprecedented concurrent realization of the unique reactivity among the methyl, methylene, and carbonyl groups in 3-methyl-5-pyrazolones for the construction of 2,3-dihydrooxepine rings. Moreover, a broad substrate scope displays a graceful diversity-oriented synthetic approach.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02182

DOI: 10.1021/acs.orglett.7b02182

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