Domino carbopalladation-cross-coupling for the synthesis of 3,3-disubstituted oxindoles

Organic Letters

Volumn 14, Issue 15, 2012, Pages 3858-3861

  Seashore Ludlow, Brinton ^a   Somfai, Peter ^a,b  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b UNIVERSITY OF TARTU   (Estonia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84864623336     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301539p     Document Type: Article

References (41)

1. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281
2. Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233-1246
3. Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010-3021
4. Gaich, T.; Baran, P. S. J. Org. Chem. 2010, 75, 4657-4673
5. Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2006.
6. Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134-7186
7. Pellissier, H. Tetrahedron 2006, 62, 2143-2173
8. Pellissier, H. Tetrahedron 2006, 62, 1619-1665
9. Tietze, L. F.; Brasche, G.; Gericke, K. M. Transition Metal-Catalyzed Domino Reactions. In Domino Reactions in Organic Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: 2006; pp 359-493.
10. Negishi, E.-i.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. (Washington, DC, U.S.) 1996, 96, 365-394
11. Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65-87
12. Seashore-Ludlow, B.; Danielsson, J.; Somfai, P. Adv. Synth. Catal. 2012, 354, 205-216
13. Seashore-Ludlow, B.; Somfai, P. Org. Lett. 2010, 12, 3732-3735
14. Yanada, R.; Obika, S.; Inokuma, T.; Yanada, K.; Yamashita, M.; Ohta, S.; Takemoto, Y. J. Org. Chem. 2005, 70, 6972-6975
15. Oh, C. H.; Lim, Y. M. Tetrahedron Lett. 2003, 44, 267-270
16. Cheung, W. S.; Patch, R. J.; Player, M. R. J. Org. Chem. 2005, 70, 3741-3744
17. Yu, H.; Richey, R. N.; Carson, M. W.; Coghlan, M. J. Org. Lett. 2006, 8, 1685-1688
18. Guo, L.-N.; Duan, X.-H.; Hu, J.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. Eur. J. Org. Chem. 2008, 1418-1425
19. Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511-2514
20. Arthuis, M.; Pontikis, R.; Florent, J.-C. Tetrahedron Lett. 2007, 48, 6397-6400
21. Marchal, E.; Cupif, J.-F.; Uriac, P.; van de Weghe, P. Tetrahedron Lett. 2008, 49, 3713-3715
22. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803-11826
23. Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803-11826
24. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003-3025
25. Klein, J. E. M. N.; Taylor, R. J. K. Eur. J. Org. Chem. 2011, 6821-6841
26. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748-8758
27. Marti, M.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219
28. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381-1407
29. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20-38
30. Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651-12666
31. Shangary, S.; Qin, D.; McEachern, D.; Liu, M.; Miller, R. S.; Qiu, S.; Nikolovska-Coleska, Z.; Ding, K.; Wang, G.; Chen, J.; Bernard, D.; Zhang, J.; Lu, Y.; Gu, Q.; Shah, R. B.; Pienta, K. J.; Ling, X.; Kang, S.; Guo, M.; Sun, Y.; Yang, D.; Wang, S. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 3933-3938
32. Antonchick, A. P.; Gerding-Reimers, C.; Catarinella, M.; Schurmann, M.; Preut, H.; Ziegler, S.; Rauh, D.; Waldmann, H. Nat. Chem. 2010, 2, 735-740
33. Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130-10131
34. Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, S.; Shangary, S.; Gao, W.; Qin, D.; Stuckey, J.; Krajewski, K.; Rooller, P. P.; Wang, S. J. Med. Chem. 2006, 49, 3432-3435
35. For a recent synthesis, see: Wu, H.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132, 14052-14054
36. For a recent synthesis, see: Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008-12011
37. For a related domino approach to these compounds, see: Evans, M. A.; Sacher, J. R.; Weinreb, S. M. Tetrahedron 2009, 65, 6712-6719
38. For example, see: Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107-109
39. Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2116-2119
40. Butters, M.; Harvey, J. N.; Jover, J.; Lennox, A. J. J.; Lloyd-Jones, G. C.; Murray, P. M. Angew. Chem., Int. Ed. 2010, 49, 5156-5160
41. Lennox, A. J. J.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2012, 134, 7431-7441