Efficient Carbamate Synthesis via a Three-Component Coupling of an Amine, CO₂, and Alkyl Halides in the Presence of Cs₂CO₃ and Tetrabutylammonium Iodide

Ralph N. Salvatore, Seung Il Shin, Advait S. Nagle and Kyung Woon Jung*

*Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, Tampa, Florida 33620-5250, USA, Email: kwjungusc.edu

R. N. Salvatore, S. Il Shin, A. S. Nagle, K. W. Jung, J. Org. Chem., 2001, 66, 1035-1037.

DOI: 10.1021/jo001140u

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Abstract

A three component coupling of amines, carbon dioxide, and halides enables an efficient synthesis of carbamates in the presence of cesium carbonate and TBAI. The method offers mild reaction conditions and short reaction times and avoids N-alkylation of the amine and overalkylation of the carbamate. In addition, chiral substrates were resistant to racemization.

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Key Words

carbamates, multicomponent reactions

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ID: J42-Y2001