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Rh(II)-Catalyzed Chemoselective Oxidative Amination and Cyclization Cascade of 1‑(Arylethynyl)cycloalkyl)methyl Sulfamates

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posted on 28.06.2017, 14:55 by Dong Pan, Yin Wei, Min Shi
A Rh­(II)-catalyzed chemoselective oxidative amination and cyclization cascade of 1-(arylethynyl)­cyclo­alkyl)­methyl sulfamates has been presented. For a cyclopropyl or cyclobutyl moiety containing alkynyl sulfamates, the reactions underwent a metallonitrene-initiated alkyne oxidation along with cyclopropyl ring expansion or alkoxyl moiety migration to give cyclobutane-fused or methylene­cyclobutane-containing heterocycles. In the case of a cyclopentyl or cyclohexyl moiety containing sulfamate, the reaction underwent a direct C–H bond insertion event to afford the corresponding nitrogen-containing heterocyclic product.