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Recyclable Hypervalent‐Iodine‐Mediated Dehydrogenative α,β′‐Bifunctionalization of β‐Keto Esters Under Metal‐Free Conditions
Authors:Ya‐Nan Duan  Li‐Qian Cui  Lin‐Hong Zuo  Chi Zhang
Institution:State Key Laboratory of Elemento‐Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China)
Abstract:We have developed a method for recyclable hypervalent‐iodine‐mediated direct dehydrogenative α,β′‐ bifunctionalization of β‐ketoesters and β‐diketones under metal‐free conditions, which affords a straightforward way to synthesize benzo‐fused 2,3‐dihydrofurans. This efficient, mild method, which has a wide substrate scope and good functional‐group tolerance, was used for the multistep synthesis of the protected aglycone of a naturally occurring phenolic glycoside. A mechanism involving Michael addition to an enone intermediate and subsequent oxidative cyclization is proposed.
Keywords:AIBX  carbonyl groups  dehydrogenative functionalization  metal‐free synthesis  reaction mechanism
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