Selective mono- and di-N-alkylation of aromatic amines with alcohols and acylation of aromatic amines using Ph3P/DDQ

Selective N-monoalkylation of aromatic amines with V and 2 alcohols and conversion of aromatic amines to amides are performed immediately and in excellent yields using triphenylphosphine (PPh3) and 2,3-dichloro-5,6- dicyanobenzoquinone (DDQ) in dichloromethane at room temperature. Symmetrical and unsymmetrical N,N-dialkylation of aromatic amines are also carried out in modest yield at room temperature by this reagent system. (C) 2009 Elsevier Ltd. All rights reserved.