A new carboxylating reagent (-CH2CN/CO2) was obtained by bubbling CO2 in a CH3CN-TEAP (tetraethy- lammonium perchlorate) solution previously electrolyzed under galvanostatic control. Organic carbamates were iso- lated from these solutions after addition of amines and an alkylating agent. In this paper, we describe the optimized conditions for the electrochemical synthesis of carbamates from amines and CO2, in mild and safe conditions, without any addition of bases, probases, or catalysts. Carbamates were isolated from primary and secondary aliphatic amines in high to excellent yields and from aromatic amines in moderate yields (dependent on the nucleophilicity of the nitrogen atom).
Feroci, M., CASADEI M., A., Palombi, L., Orsini, M., Inesi, A. (2003). Cyanomethyl Anion/Carbon dioxide System: An electrogenerated carboxylating reagent. Synthesis of carbamates under mild and safe conditions. JOURNAL OF ORGANIC CHEMISTRY, 68, 1548-1551.
Cyanomethyl Anion/Carbon dioxide System: An electrogenerated carboxylating reagent. Synthesis of carbamates under mild and safe conditions
ORSINI, MONICA;
2003-01-01
Abstract
A new carboxylating reagent (-CH2CN/CO2) was obtained by bubbling CO2 in a CH3CN-TEAP (tetraethy- lammonium perchlorate) solution previously electrolyzed under galvanostatic control. Organic carbamates were iso- lated from these solutions after addition of amines and an alkylating agent. In this paper, we describe the optimized conditions for the electrochemical synthesis of carbamates from amines and CO2, in mild and safe conditions, without any addition of bases, probases, or catalysts. Carbamates were isolated from primary and secondary aliphatic amines in high to excellent yields and from aromatic amines in moderate yields (dependent on the nucleophilicity of the nitrogen atom).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
