N-heterocyclic carbene and cyclic (alkyl)(amino)carbene adducts of plumbanes and plumbylenes

Abstract

Lewis-acid/base adducts of N-heterocyclic carbenes (NHCs) and the cyclic (alkyl)(amino)carbene cAAC^Me (1-(2,6-di-iso-propylphenyl)-3,3,5,5-tetramethyl-pyrrolidin-2-ylidene) with selected lead(II) and lead(IV) compounds are presented. The reaction of the NHCs Me₂Im^Me (1,3,4,5-tetramethyl-imidazolin-2-ylidene), iPr₂Im^Me (1,3-di-isopropyl-4,5-dimethyl-imidazolin-2-ylidene), Dipp₂Im (1,3-bis-(2,6-di-isopropylphenyl)-imidazolin-2-ylidene) and cAAC^Me (1-(2,6-di-iso-propylphenyl)-3,3,5,5-tetramethyl-pyrrolidin-2-ylidene) with PbI₂ yielded the NHC-containing plumbylenes NHC·PbI₂ (NHC = Me₂Im^Me (1), iPr₂Im^Me (2), Dipp₂Im (3) and cAAC^Me·PbI₂ (4)). Using the Pb(IV) compound PbCl₂Ph₂, the plumbane adducts NHC·PbCl₂Ph₂ (NHC = Me₂Im^Me (5), iPr₂Im^Me (6), Dipp₂Im (7)) and cAAC^Me·PbCl₂Ph₂ (8)) were isolated in high yields. Reduction of the lead(IV) adducts 5 and 6 with excess KC₈ afforded the diaryl substituted plumbylenes Me₂Im^Me·PbPh₂ (9) and iPr₂Im^Me·PbPh₂ (10), which are stable in the solid state but decompose in solution.