Cu-catalysed Chan–Evans–Lam reaction meets deep eutectic solvents: efficient and selective C–N bond formation under aerobic conditions at room temperature‡
Literature Information
Luciana Cicco, Paola Vitale, Filippo Maria Perna, Joaquín García-Álvarez
An unprecedented, simple and general protocol for the selective formation of C–N bonds was developed by using cheap and easily available Cu(OAc)2 as catalyst for the Cu(II)-catalysed Chan–Evans–Lam reaction in Deep Eutectic Solvents (DESs) as sustainable reaction media. The meticulous selection of both components of DES for this transformation (1ChOAc/2Urea) allows C–N coupling reactions under bench-type conditions (room temperature/under air), and in the absence of external ligands. The use of DES also permits to: (i) recycle the catalytic system for up to four consecutive runs; (ii) scale-up the C–N coupling reaction (without erosion of the yield); and (iii) apply this methodology to the synthesis of the anti-inflammatory drug Flufenamic acid (E-factor: 10).
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