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- Publisher
- Wiley
- Copyright
- Copyright © 2009 Wiley Subscription Services, Inc., A Wiley Company
- ISSN
- 0947-6539
- eISSN
- 1521-3765
- DOI
- 10.1002/chem.200900615
- pmid
- 19621394
- Publisher site
- See Article on Publisher Site
Abstract
We describe a new family of uronium‐type coupling reagents that differ in their iminium moieties and leaving groups. The presence of the morpholino group in conjunction with an oxime derivative—especially ethyl 2‐cyano‐2‐(hydroxyimino)acetate (Oxyma)—had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt derived from Oxyma (COMU) performed extremely well in the presence of only 1 equiv of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. COMU also showed a less hazardous safety profile than the benzotriazole‐based HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions. Furthermore, the Oxyma moiety contained in COMU suggests a lower risk of explosion than in the case of the benzotriazole derivatives.
Journal
Chemistry - A European Journal – Wiley
Published: Sep 21, 2010
Keywords: ; ; ; ;