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).
Cu-Catalysed Chan-Evans-Lam Reaction Meets Deep Eutectic Solvents: Efficient and selective C–N Bond Formation under Aerobic Conditions at Room Temperature
Cicco, Luciana;Vitale, Paola;Perna, Filippo M.;Capriati, Vito
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2023-01-01
Abstract
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).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
