Journal
TETRAHEDRON LETTERS
Volume 49, Issue 36, Pages 5279-5282Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.06.096
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Funding
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Environmental Science and Technology Alliance of Canada
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A convenient protocol for the parallel solution-phase synthesis of a library of thiocarbamates, ureas, carbamates, and amides from carbamoylimidazolium salts has been developed. The crystalline carbamoylimidazolium salts are readily synthesized from secondary amines, CDI and iodomethane, and act as stable carbamoylation reagents. A common set of reaction conditions and a straightforward non-chromatographic liquid-liquid extraction purification protocol were developed for reactions with thiols, amines, phenols, and carboxylic acids, giving the products with high purities and yields. The resultant library incorporates diversity arising from the choice of reaction partners and the functional group linkage generated in the couplings. (C) 2008 Published by Elsevier Ltd.
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