Zinc(II)-Mediated Carbene Insertion into C–H Bonds in Alkanes

The cationic zinc adduct {[HB­(3,5-(CF3)2Pz)3]­Zn­(NCMe)2}­ClO4 catalyzes the functionalization of tertiary, secondary, and primary C–H bonds of alkanes via carbene insertion. Ethyl diazoacetate serves as the :CHCO2Et carbene precursor. The counteranion, supporting ligand, and coordinating solvents affect the catalytic activity. An in situ generated {[HB­(3,5-(CF3)2Pz)3]­Zn}+ species containing a bulkier {B­[3,5-(CF3)2C6H3]4}− anion gives the best results among the zinc catalysts used.