Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonatesElectronic supplementary information (ESI) available: Full experimental procedures and characterisation, as well as 1H and 13C NMR spectra for novel compounds. See DOI: 10.1039/c4ob02629b

Triazolinylidenes promote γ-selective C-carboxylation (up to 99 : 1 regioselectivity) in the O - to C -carboxyl transfer of furanyl carbonates in contrast to DMAP that promotes preferential α-C-carboxylation with moderate regiocontrol (typically 60 : 40 regioselectivity). The generality of this process is described and a simple mechanistic and kinetic model postulated to account for the observed regioselectivity Triazolinylidenes promote γ-selective C-carboxylation (up to 99 : 1 regioselectivity) in the O - to C -carboxyl transfer of furanyl carbonates in contrast to DMAP that promotes preferential α-C-carboxylation with moderate regiocontrol (typically 60 : 40 regioselectivity).