This research was supported by the Institute of Bioengineering and Nanotechnology, Biomedical Research Council, Agency for Science, Technology and Research, Singapore.
Acetylide Ion (C22−) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis†
Article first published online: 10 APR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 19, pages 5125–5128, May 3, 2013
How to Cite
Yu, D., Sum, Y. N., Ean, A. C. C., Chin, M. P. and Zhang, Y. (2013), Acetylide Ion (C22−) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis . Angew. Chem. Int. Ed., 52: 5125–5128. doi: 10.1002/anie.201301019
- Issue published online: 10 MAY 2013
- Article first published online: 10 APR 2013
- Manuscript Revised: 8 MAR 2013
- Manuscript Received: 5 FEB 2013
- acetylide ion;
- calcium carbide;
- sustainable chemistry
Friendly competition: A three-component reaction system composed of calcium carbide, an aryl aldehyde, and an amine gave enaminones or propargylamines (see picture) in a predictable manner through competitive pathways. The system enables the cost-efficient synthesis of a variety of enaminones from readily accessible small molecules and demonstrates the versatility of the acetylide ion, which can be used to bridge electrophiles and nucleophiles.