Organic Letters
Organic Letters
4 years ago

Tunable Aerobic Oxidative Hydroxylation/Dehydrogenative Homocoupling of Pyrazol-5-ones under Transition-Metal-Free Conditions

Tunable Aerobic Oxidative Hydroxylation/Dehydrogenative Homocoupling of Pyrazol-5-ones under Transition-Metal-Free Conditions
Gaoxi Jiang, Jinlong Zhang, Huameng Yang, Xuguang Sheng
A practical and tunable transition-metal-free aerobic oxidation of pyrazol-5-ones preparing either 4-hydroxypyrazoles (via C–H hydroxylation) or bispyrazoles (via dehydrogenative homocoupling) is described. The K2CO3/dioxane reagent system predominately promoted hydroxylation to deliver the α-hydroxylated pyrazoles. In contrast, the formation of bispyrazoles was overwhelmingly preferred with CH3CN as the reaction medium without any additives.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00951

DOI: 10.1021/acs.orglett.7b00951

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