Dealuminated H-Y zeolites generate, stabilize and catalytically insert carbenes from diazocarbonyl compounds

Abstract

[EN] Carbenes are among the most powerful reactants in organic synthesis, with capacity to insert into a variety of otherwise stable bonds, and generate two new bonds in a straightforward manner. However, the intrinsic instability of such carbenes makes them to be catalytically generated, in-situ, from precursors such as diazocarbonyl compounds, and the catalyst, in turn, also controls the subsequent insertion reaction. The catalyst is generally a metal complex in solution, mainly Cu, Ag or Rh, but also others, including protons in rare cases. Here we show that carbenes are generated, stabilized and inserted into C-C, C-H, O-H, N-H, Si-H and O-O bonds after reacting diazocarbonyl compounds with catalytic amounts of metal-free, commercially available dealuminated H-Y zeolites. These results open the way to design carbene-mediated organic reactions on readily available and reusable catalytic solids without involving metals.