Electrochemically Promoted C−N Bond Formation from Amines and CO2 in Ionic Liquid BMIm−BF4:  Synthesis of Carbamates

M. Feroci,*† M. Orsini,† L. Rossi,‡ G. Sotgiu,§ and A. Inesi*†;
Dipartimento di Ingegneria Chimica, Materiali, Materie Prime e Metallurgia, Universit La Sapienza, via Castro Laurenziano, 7, I-00161 Roma, Italy, Dipartimento di Chimica, Ingegneria Chimica e Materiali, Universit degli Studi, I-67040 Monteluco di Roio, L'Aquila, Italy, and Dipartimento di Elettronica Applicata, Universit di Roma Tre, via Vasca Navale, 84, I-00146 Roma, Italy
J. Org. Chem., 2007, 72 (1), pp 200–203
DOI: 10.1021/jo061997c
Publication Date (Web): December 7, 2006
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Università “La Sapienza”.

,
‡

 Università degli Studi.

,
§

 Università di Roma Tre.

, marta.feroci@uniroma1.it, ; , achille.inesi@uniroma1.it

Abstract

Abstract Image

A new electrochemical procedure for the synthesis of organic carbamates from amines and carbon dioxide has been developed using selective cathodic reduction of carbon dioxide in CO2-saturated room-temperature ionic liquid BMIm-BF4 solutions containing amines 1a−j, followed by addition of EtI as an alkylating agent. The synthesis was carried out under mild (PCO2 = 1.0 atm, t = 55 °C) and safe conditions, and the use of volatile and toxic solvents and catalysts (according to the growing demand for ecofriendly synthetic methodologies), as well as of any supporting electrolyte (for a very easy workup of the reaction mixture), was avoided. Carbamates 2a−j were isolated in good to high yields.

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History

  • Published In Issue January 05, 2007
  • Received September 28, 2006

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