Palladium-catalyzed [3+2+1] cyclocarbonylative coupling of 1,3-cyclohexanediones, alkynes, and carbon monoxide: An atom-economic route to chromene-2,5-dione derivatives

Tetrahedron Letters

Volumn 51, Issue 49, 2010, Pages 6433-6435

  Wu, Bei ^a,b   Hua, Ruimao ^a,b  

^a TSINGHUA UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

1,3 Cyclohexanediones; Alkynes; Carbon monoxide; Chromene 2,5 dione; Palladium

Indexed keywords

ALKYNE; CARBON MONOXIDE; CARBONYL DERIVATIVE; CHROMENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; ENANTIOSELECTIVITY;

EID: 78149280136     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.132     Document Type: Article

References (19)

1. Selected reviews, see: G.H. Posner Chem. Rev. 86 1986 831 844
2. D.J. Ramón, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602 1634
3. B. Ganem Acc. Chem. Res. 42 2009 463 472
4. Selected reviews, see: M. Lautens, W. Klute, and W. Tam Chem. Rev. 96 1996 49 92
5. S. Saito, and Y. Yamamoto Chem. Rev. 100 2000 2901 2915
6. J.A. Varela, and C. Saá Chem. Rev. 103 2003 3787 3801
7. I. Nakamura, and Y. Yamamoto Chem. Rev. 104 2004 2127 2198
8. Selected recent reports, see: S. Ma, B. Wu, X. Jiang, and S. Zhao J. Org. Chem. 70 2005 2568 2575
9. Y. Li, Z. Yu, and H. Alper Org. Lett. 9 2007 1647 1649
10. K. Itoh, and S. Kanemasa Tetrahedron Lett. 44 2003 1799 1802
11. M.G. Ahmed, S.A. Ahmed, M.K. Uddin, M.T. Rahman, U.K.R. Romman, M. Fujio, and Y. Tsuda Tetrahedron Lett. 46 2005 8217 8220
12. A.V. Kurdyumov, N. Lin, R.P. Hsung, G.C. Gullickson, K.P. Cole, N. Sydorenko, and J. Swidorski J. Org. Lett. 8 2006 191 193
13. J. Li, W. Tang, L. Lu, and W. Su Tetrahedron Lett. 49 2008 7117 7120
14. A. Garcia, D. Borchardt, C.-E.A. Chang, and M.J. Marsella J. Am. Chem. Soc. 131 2009 16640 16641
15. Q. Huang, and R. Hua Catal. Commun. 8 2007 1031 1035
16. Q. Huang, and R. Hua Chem. Eur. J. 13 2007 8333 8337
17. Q. Huang, and R. Hua Chem. Eur. J. 15 2009 3817 3822
18. 4, the reactions were first carried out using an excess amount of 2a.
19. 2, CCDC785612 (3a), and CCDC785613 (3j) contain Supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk.