title: Recyclable Hypervalent-Iodine-Mediated Dehydrogenative α,β'-Bifunctionalization of β-Keto Esters Under Metal-Free Conditions.
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.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China).
authors.forename: Ya-Nan
authors.initials: YN
authors.lastname: Duan
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China).
authors.forename: Li-Qian
authors.initials: LQ
authors.lastname: Cui
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China).
authors.forename: Lin-Hong
authors.initials: LH
authors.lastname: Zuo
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071 (P. R. China). zhangchi@nankai.edu.cn.
authors.forename: Chi
authors.initials: C
authors.lastname: Zhang
keywords: AIBX; carbonyl groups; dehydrogenative functionalization; metal-free synthesis; reaction mechanism