Fluoro-functionalized polymeric N-heterocyclic carbene-zinc complexes: efficient catalyst for formylation and methylation of amines with CO2 as a C1-building block?

RSC Advances Pub Date: 2015-02-11 DOI: 10.1039/C5RA00380F

Abstract

A fluoro-functionalized polymeric N-heterocyclic carbene (NHC)-Zn complex (F-PNHC-Zn) was designed and synthesized by taking fluorous imidazolium salts as precursors through a two-step alkylation. The resultant F-PNHC-Zn was applied in catalyzing the formylation and methylation of amines using CO2 as a C1 building block in the presence of organosilane, which showed much higher activity than the corresponding non-fluorous PNHC-Zn under identical conditions. N-Methylanilines with both electron-withdrawing and electron-donating groups all could be converted to the corresponding formamides and methylamines in >90% conversion. Quantitative conversion of N-methylaniline was obtained even under very low CO2 pressure (0.05 MPa diluted by N2). Moreover, F-PNHC-Zn was highly stable and easily recyclable for these reactions.

Graphical abstract: Fluoro-functionalized polymeric N-heterocyclic carbene-zinc complexes: efficient catalyst for formylation and methylation of amines with CO2 as a C1-building block
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