[3 + 2] cycloaddition and subsequent oxidative dehydrogenation between alkenes and diazo compounds: a simple and direct approach to pyrazoles using TBAI/TBHP?

Organic & Biomolecular Chemistry Pub Date: 2016-08-15 DOI: 10.1039/C6OB01522K

Abstract

A novel Bu4NI-catalyzed pyrazole formation reaction is well described via sequential [3 + 2] cycloaddition and oxidative dehydrogenation reactions using TBHP as the primary oxidant. In comparison with previous cases toward pyrazoles from alkenes and diazo compounds, alkenes without a pre-organized leaving group were applied in this transformation. In addition, this methodology was distinguished by its broad substrate scope, commercially available inexpensive starting materials, high atom economy and operational simplicity.

Graphical abstract: [3 + 2] cycloaddition and subsequent oxidative dehydrogenation between alkenes and diazo compounds: a simple and direct approach to pyrazoles using TBAI/TBHP
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