Ruthenium-Catalyzed Intramolecular [2+2+2] Cycloaddition and Tandem Cross-Metathesis of Triynes and Enediynes
Article first published online: 19 FEB 2013
© 2013. The Authors. ChemistryOpen published by WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
Volume 2, Issue 2, pages 63–68, April 2013
How to Cite
Yuan, W., Wei, Y. and Shi, M. (2013), Ruthenium-Catalyzed Intramolecular [2+2+2] Cycloaddition and Tandem Cross-Metathesis of Triynes and Enediynes. ChemistryOpen, 2: 63–68. doi: 10.1002/open.201300002
- Issue published online: 23 APR 2013
- Article first published online: 19 FEB 2013
- Manuscript Received: 22 JAN 2013
- Funded Access
- Shanghai Municipal Committee of Science and Technology. Grant Number: 11JC1402600
- National Basic Research Program of China. Grant Number: (973)-2009CB825300
- National Natural Science Foundation of China. Grant Numbers: 21102166, 20872162, 21072206, 20672127, 21121062, 20732008
- first-generation Grubbs catalyst;
[2+2+2] Cycloadditions can be applied to specifically build up derivatives of benzene and cyclohexadiene and, therefore, have attracted much attention. Herein, we present an intramolecular [2+2+2] cycloaddition of triynes catalyzed by the first-generation Grubbs ruthenium complex (Ru gen-1), which can efficiently afford benzene derivatives in good yields under mild conditions. Moreover, we also report on a novel tandem cross-metathesis transformation of intramolecular enediynes also catalyzed by Ru gen-1, which has not been observed previously in related reports. On the basis of deuterium labeling experiments, a possible reaction mechanism is presented.