Amidations Using N,N ‘-Carbonyldiimidazole: Remarkable Rate Enhancement by Carbon Dioxide
- 3 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (7), 2565-2568
- https://doi.org/10.1021/jo049949k
Abstract
Carbon dioxide catalyzes the reaction of imidazolides with amines to form amides. A substantial rate enhancement is observed in the presence of CO(2) compared to the CO(2)-free case. The scope and limitations of this reaction are discussed.Keywords
This publication has 11 references indexed in Scilit:
- Early Amidation Approach to 3-[(4-Amido)pyrrol-2-yl]-2-indolinonesThe Journal of Organic Chemistry, 2003
- Reversible covalent chemistry of CO2Chemical Communications, 2002
- Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAITetrahedron, 2002
- Carbon Dioxide as a Phosgene Replacement: Synthesis and Mechanistic Studies of Urethanes from Amines, CO2, and Alkyl ChloridesThe Journal of Organic Chemistry, 1995
- Highly selective generation of urethanes from amines, carbon dioxide and alkyl chloridesJournal of the Chemical Society, Chemical Communications, 1994
- Role of the macrocyclic polyether in the synthesis of N-alkylcarbamate esters from primary amines, CO2 and alkyl halides in the presence of crown-ethers.Tetrahedron, 1992
- Alkali-metal-assisted transfer of the carbamate group from phosphocarbamates to alkyl halides: a new easy way to alkali-metal carbamates and to carbamate estersJ. Chem. Soc., Dalton Trans., 1992
- Mechanistic studies on the role of carbon dioxide in the synthesis of methylcarbamates from amines and dimethylcarbonate in the Presence of CO2.Tetrahedron, 1991
- Novel Synthesis of Carbamate Ester from Carbon Dioxide, Amines, and Alkyl HalidesBulletin of the Chemical Society of Japan, 1989
- Reactivity of phosphacarbamates: transfer of the carbamate group promoted by metal-assisted electrophilic attack at the carbon dioxide moietyThe Journal of Organic Chemistry, 1988