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An efficient regioselective sp3 C–H azidation is developed using CuBr as the catalyst and Zhdankin azidoiodinane as the “N3” source. Under simple and mild reaction conditions, the azido group could be successfully incorporated into the sp3 C–H alkyl substituents of indoles and tetrahydrocarbazoles.

A convenient and efficient approach for the difunctionalization of alkenylpyridine N-oxides through the tandem addition/Boekelheide rearrangement has been developed. The C–O and C–X (S, O, Cl) bonds are constructed simultaneously at the α- and β-positions under mild reaction conditions in 100% atom economy, which complements previously reported α- or β-functionalizations.

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