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Short Paper | Special issue | Vol 97, No. 1, 2018, pp.632-645
Published online, 12th April, 2018
DOI: 10.3987/COM-18-S(T)52
Metal-Free Oxidative Cross-Coupling of Pyrroles with Electron-Rich Arenes Using Recyclable Hypervalent Iodine(III) Reagent

Koji Morimoto, Toru Kamitanaka, Toshifumi Dohi, and Yasuyuki Kita*

*Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan


The facile and clean oxidative cross-coupling reaction of pyrroles has been developed using the recyclable hypervalent iodine(III) reagents having an adamantane core. The recyclable iodine(III) reagent could be recovered from the reaction mixtures as the corresponding reduced forms, i.e., the tetraiodide 2, by a simple solid-liquid separation. By re-oxidizing the recovered 2 to the initial reagent 1a using m-chloroperbenzoic acid (mCPBA), the reagent 1a can be reused.