Palladium-catalyzed carbonylative sonogashira coupling of aryl bromides using near stoichiometric carbon monoxide

Organic Letters

Volumn 16, Issue 8, 2014, Pages 2216-2219

  Neumann, Karoline T ^a   Laursen, Simon R ^a   Lindhardt, Anders T ^b   Bang Andersen, Benny ^c   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

^c H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BROMINATED HYDROCARBON; CARBON; CARBON MONOXIDE; CHLORINATED HYDROCARBON; KETONE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; CARBON ISOTOPES; CARBON MONOXIDE; CATALYSIS; HYDROCARBONS, BROMINATED; HYDROCARBONS, CHLORINATED; KETONES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84898968032     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5007289     Document Type: Article

References (48)

1. Karpov, A. S.; Merkul, E.; Rominger, F.; Müller, T. J. J. Angew. Chem. 2005, 117, 7112
2. Souza, D. M. D.; Müller, T. J. J. Nat. Protoc. 2008, 3, 1660
3. Marco-Contelles, J.; Opazo, E. J. Org. Chem. 2002, 67, 3705
4. Forsyth, C. J.; Xu, J.; Nguyen, S. T.; Samdai, I. A.; Briggs, L. R.; Rundberget, T.; Sandvik, M.; Miles, C. O. J. Am. Chem. Soc. 2006, 128, 15114
5. Tietze, L. F.; Singidi, R. R.; Gericke, K. M.; Bockemeier, H.; Laatsch, H. Eur. J. Org. Chem. 2007, 5875
6. Liu, H.; Jiang, H.; Zhang, M.; Yao, W.; Zhu, Q.; Tang, Z. Tetrahedron Lett. 2008, 49, 3805
7. Willy, B.; Müller, T. J. J. ARKIVOC 2008, 195
8. Bagley, M. C.; Dale, J. W.; Bower, J. Synlett 2001, 1149
9. Karpov, A. S.; Müller, T. J. J. Synthesis 2003, 2815
10. Willy, B.; Dallos, T.; Rominger, F.; Schönhaber, J.; Müller, T. J. J. Eur. J. Org. Chem. 2008, 4796
11. Lee, K. Y.; Lee, M. J.; Kim, J. N. Tetrahedron 2005, 61, 8705
12. Stefani, H. A.; Cella, R.; Dorr, F. A.; de Pereira, C. M. P.; Gomes, F. P.; Zeni, G. Tetrahedron Lett. 2005, 46, 2001
13. Palimkar, S. S.; Kumar, P. H.; Jogdand, N. R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron Lett. 2006, 47, 5527
14. Yim, S. J.; Kwon, C. H.; An, D. K. Tetrahedron Lett. 2007, 48, 5393
15. Jackson, M. M.; Leverett, C.; Toczko, J. F.; Roberts, J. C. J. Org. Chem. 2002, 67, 5032
16. Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2004, 69, 1615
17. Wang, B.; Bonin, M.; Micouin, L. J. Org. Chem. 2005, 70, 6126
18. Chen, L.; Li, C. Org. Lett. 2004, 6, 3151
19. Kakusawa, N.; Yamaguchi, K.; Kurita, J.; Tsuchiya, T. Tetrahedron Lett. 2000, 41, 4143
20. Taylor, C.; Bolshan, Y. Org. Lett. 2014, 16, 488
21. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1
22. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Soc. Rev. 2011, 40, 4986
23. Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem. 2009, 121, 4176
24. Angew. Chem., Int. Ed. 2009, 48, 4114.
25. Brennführer, A.; Neumann, H.; Beller, M. ChemCatChem 2009, 1, 28
26. Skoda-Foldes, R.; Kollár, L. Curr. Org. Chem. 2002, 6, 1097
27. Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: New York, 1995.
28. Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. A: Chem. 1995, 104, 17
29. Liu, J.; Peng, X.; Sun, W.; Zhao, Y.; Xia, C. Org. Lett. 2008, 10, 3933
30. Mohamed Ahmed, M. S.; Mori, A. Org. Lett. 2003, 5, 3057
31. Liu, J.; Chen, J.; Xia, C. J. Catal. 2008, 253, 50
32. Kang, S.; Lim, K.; Ho, P.; Kim, W. Synthesis 1997, 874
33. Delaude, L.; Masdeu, A. M.; Alper, H. Synthesis 1994, 1149
34. Arcadi, A.; Cacchi, S.; Marinelli, F.; Pace, P.; Sanzi, G. Synlett 1995, 823
35. Iizuka, M.; Kondo, Y. Eur. J. Org. Chem. 2007, 5180
36. Kobayashi, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1981, 333
37. Sans, V.; Trzeciak, A. M.; Luis, S.; Ziólkowski, J. J. Catal. Lett. 2006, 109, 37
38. Fukuyama, T.; Yamaura, R.; Ryu, I. Can. J. Chem. 2005, 83, 711
39. Rahman, M. T.; Fukuyama, T.; Kamata, N.; Sato, M.; Ryu, I. Chem. Commun. 2006, 2236
40. Liang, B.; Huang, M.; You, Z.; Xiong, Z.; Lu, K.; Fathi, R.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 6097
41. Fusano, A.; Fukuyama, T.; Nishitani, S.; Inouye, T.; Ryu, I. Org. Lett. 2010, 12, 2410
42. Tambade, P. J.; Patil, Y. P.; Nandurkar, N. S.; Bhanage, B. M. Synlett 2008, 886
43. Wu, X.-F.; Neumann, H.; Beller, M. Chem. Eur. J. 2010, 16, 12104
44. Hermange, P.; Lindhardt, A. T.; Taaning, R. H.; Bjerglund, K.; Lupp, D.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 6061
45. Friis, S. D.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 133, 18114
46. Nielsen, D. U.; Lescot, C.; Lindhardt, A. T.; Gøgsig, T. M.; Skrydstrup, T. Chem. Eur. J. 2013, 19, 17926 and references cited therein.
47. Korsager, S.; Taaning, R. H.; Lindhardt, A. T.; Skrydstrup, T. J. Org. Chem. 2013, 78, 6120
48. Ward, T. R.; Turunen, B. J.; Haack, T.; Neuenswander, B.; Shadrick, W.; Georg, G. I. Tetrahedron Lett. 2009, 50, 6494