Recyclable Hypervalent‐Iodine‐Mediated Dehydrogenative α,β′‐Bifunctionalization of β‐Keto Esters Under Metal‐Free Conditions |
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Authors: | Ya‐Nan Duan Li‐Qian Cui Lin‐Hong Zuo Chi Zhang |
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Institution: | State Key Laboratory of Elemento‐Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China) |
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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. |
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Keywords: | AIBX carbonyl groups dehydrogenative functionalization metal‐free synthesis reaction mechanism |
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