N -acylsulfonamide assisted tandem C-H olefination/annulation: Synthesis of isoindolinones

Organic Letters

Volumn 13, Issue 5, 2011, Pages 1214-1217

  Zhu, Chen ^a   Falck, J R ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; INDOLE DERIVATIVE; KETONE; SULFONAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDOLES; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONAMIDES;

EID: 79952182385     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200093f     Document Type: Article

References (57)

1. For initial reports, see: Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119
2. Fujiwara, Y.; Moritani, I.; Matsuda, M.; Teranishi, S. Tetrahedron Lett. 1968, 9, 633
3. For reviews, see: Moritani, I.; Fujiwara, Y. Synthesis 1973, 524
4. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
5. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
6. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
7. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
8. Trost, B. M.; Godleski, S. A.; Genêt, J. P. J. Am. Chem. Soc. 1978, 100, 3930
9. Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1993, 115, 9323
10. Baran, P. S.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 7904
11. Garg, N. K.; Caspi, D. D.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 9552
12. Beck, E. M.; Hatley, R.; Gaunt, M. J. Angew. Chem., Int. Ed. 2008, 47, 3004
13. For examples of Pd(II) catalyzed C-H olefination with directing groups, see: Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586
14. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156
15. Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666
16. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254
17. Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066
18. García-Rubia, A.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 6511.
19. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
20. Shi, B. F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460
21. Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 6169
22. Nishikata, T.; Lipshutz, B. H. Org. Lett. 2010, 12, 1972
23. García-Rubia, A.; Urones, B.; Arrayás, R. G.; Carretero, J. C. Chem.-Eur. J. 2010, 16, 9676
24. For examples of Pd(II) catalyzed C-H olefinations without directing groups, see: Fujiwara, Y.; Maruyama, O.; Yoshidomi, M.; Taniguchi, H. J. Org. Chem. 1981, 46, 851
25. Itahara, T.; Ikeda, M.; Sakakibara, T. J. Chem. Soc., Perkin Trans. 1 1983, 1361
26. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578
27. Beccalli, E. M.; Broggini, G. Tetrahedron Lett. 2003, 44, 1919
28. Ma, S.; Yu, S. Tetrahedron Lett. 2004, 45, 8419
29. Liu, C.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 10250
30. Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125
31. Zhang, X.; Fan, S.; He, C.-Y.; Wan, X.; Min, Q.-Q.; Yang, J.; Jiang, Z.-X. J. Am. Chem. Soc. 2010, 132, 4506
32. Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211 Also see: Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
33. Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362
34. Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452
35. Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916
36. 3)-H olefination/C-N formation, see: Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680
37. See Supporting Information for details of reaction parameter screening.
38. 2 as an oxidant in C-H olefination, see: Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
39. Engle, K. M.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137
40. For mechanistic studies of Pd(II)-mediated C-H cleavages, see: Ryabov, A. D.; Sakodinskaya, I. K.; Yatsimirsky, A. K. J. Chem. Soc., Dalton Trans. 1985, 2629
41. Canty, A. J.; van Koten, G. Acc. Chem. Res. 1995, 28, 406
42. Gómez, M.; Granell, J.; Martinez, M. Organometallics 1997, 16, 2539
43. Gómez, M.; Granell, J.; Martinez, M. J. Chem. Soc., Dalton Trans. 1998, 37
44. Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 2000, 19, 3895
45. Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754
46. Tunge, J. A.; Foresee, L. N. Organometallics 2005, 24, 6440
47. Davidson, J. M.; Triggs, C. J. Chem. Soc. A 1968, 1324
48. Shue, R. S. J. Am. Chem. Soc. 1971, 93, 7116
49. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050
50. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581
51. For examples of Pd(II)-mediated C-H activation involving benzamides, see: Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655
52. Shabashov, D.; Daugulis, O. Org. Lett. 2006, 8, 4947
53. Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190
54. Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058
55. Yeung, C. S.; Zhao., X.; Borduas, N.; Dong, V. M. Chem. Sci. 2010, 1, 331
56. Trend, R. M.; Ramtohul, Y. K.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 17778
57. Formation of byproduct isoquinolinone 6 was not observed in the experiment. It presumably derived from intermediate II via reductive elimination and subsequent dehydrogenation.