Facile Chan‐Lam coupling using ferrocene tethered N‐heterocyclic carbene‐copper complex anchored on graphene

Abstract

Ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of graphene followed by metallation with copper (I) iodide. The [GrFemImi]NHC@Cu complex has been characterized by fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), CP-MAS 13 C NMR spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), energy dispersive Xray (EDX) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer-Emmett-Teller (BET) surface area analysis and X-ray diffractometer (XRD) analysis. This novel complex served as a robust heterogeneous catalyst for the synthesis of bioactive N-aryl sulfonamides from variety of aryl boronic acids and sulfonyl azides in ethanol by Chan-Lam coupling. Recyclability experiments were executed successfully for six consecutive runs.

[Cell@Al2O3(HEPiPY)]DCA: A Cellulose Supported Ionic Liquid Catalyst for Synthesis of 11 b,12‐dihydro‐6H,13Hbenzo[5,6][1,3]oxazino[3,4‐a]quinazoline‐6,13‐dione along with in silico assessments

“…[27] The absence of CÀ Cl band at 682 cm À 1 demonstrated successful qua ternization and formation of [Cell@Al 2 O 3 (HEPiPY)]Cl. [28] The synthesis of [Cell@Al 2 O 3 (HEPiPY)]DCA was confirmed by presence of characteristic peaks at 2375 cm À 1 and 2324 cm À 1 for N(CN) 2 (Figure 2c). The elemental composition of the catalyst was investigated by energy dispersive X-ray (EDX) analysis.…”

Bypassing Sulfonyl Halides: Synthesis of Sulfonamides from Other Sulfur‐Containing Building Blocks

“…[104] In this case, CuCl was used as an efficient catalyst providing high yields of secondary sulfonamides at mild conditions (MeOH, rt, air) for a wide range of compounds (Scheme 43). After this publication, other groups have also studied similar transformations for the sulfonamide synthesis using various copper catalysts, i. e., CuCl, [105] [Cu(DMAP) 4 I]I, [106] [MCM-41-L-proline-CuCl], [107] [GrFemImi]NHC@Cu, [108] or CuCl 2 @PAN PA-2 F. [109] Furthermore, sulfonyl azides have been widely used in transition-metal-catalyzed site-selective (hetero)aromatic CÀ H sulfonamidations (Scheme 44). The reader is referred to a recent review by Vessally and co-workers that covered this type of transformation in detail.…”

Carbon–nitrogen bond formation using modified graphene oxide derivatives decorated with copper complexes and nanoparticles

“…Ferrocene tethered N ‐heterocyclic carbene–copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) was applied in Chan–Lam coupling reaction. [ 60 ] [GrFemImi]NHC@Cu complex was prepared using covalent insertion of ferrocenyl ionic liquid on graphene followed by metalation with CuI. The catalytic activity of [GrFemImi]NHC@Cu catalyst was investigated in N ‐arylation of sulfonamides through the reaction of various phenylboronic acids with sulfonyl azides under reflux conditions during 45–660 min (Scheme 11).…”