C-N Bond Formation Using Polyaniline Nanofibers Supported CuI

Significance

The polyaniline nanofiber supported CuI (CuI-PANInf) complex was found to promote the N-arylation of aliphatic, aromatic, and heterocyclic amines with aryl halides. Thus, poly­aniline nanofibers (PANInf) were prepared using sol-gel technique with chemical oxidation according to the reported procedures (J. Am. Chem. Soc. 2004, 126, 851). The reaction of PANInf with CuI gave CuI-PANInf 1. The N-arylation was performed with 1-iodo-2-nitrobenzene (2a) and pentylamine (3a) in the presence of CuI-PANInf 1 (5 mol% copper) to give the 2-nitro-N-pentylaniline (4a) in 99% yield. The CuI-PANInf 1 was recovered and reused without loss of its catalytic activity.