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A novel transformation is reported for the reaction of terminal or internal alkynes with the nitrene precursor PhI=NTs (Ts=p-toluenesulfonyl) in the presence of catalytic amounts of Tp Cu(NCMe) (Tp =hydrotris(3,4,5-tribromo-pyrazolylborate). Two products containing an imine functionality have been isolated from the reaction mixtures, identified as sulfinamides and isothiazoles. The former correspond to the formal reduction of the sulfone group into sulfoxide, whereas the latter involves the insertion of an alkyne carbon atom into the aromatic ring of the N-tosyl moiety.

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A series of alkanes CnH2n+2 have been functionalized in water as the reaction medium, using a silver-based catalyst, upon insertion of carbene (CHCO2Et from N2CHCO2Et) groups into their carbon-hydrogen bonds of hexane, cyclohexane or 2-methylbutane, among others. The regioselectivity toward the distinct reaction sites is identical to that found in neat alkane, the water-based system allowing the use of a much shorter excess of the hydrocarbon. This is the first example of the intermolecular functionalization of alkanes with this strategy in water. The functionalized alkanes partially undergoes a incorporation of a second carbene unit to provide -(acyloxy)acetates, in an unprecedented tandem reaction of this nature.