Synthesis of oxindole-3-acetates through iron-catalyzed oxidative arylalkoxycarbonylation of activated alkenes

Tetrahedron

Volumn 70, Issue 21, 2014, Pages 3466-3470

  Wang, Gao ^a   Wang, Shan ^a   Wang, Jian ^a   Chen, Shan Yong ^a   Yu, Xiao Qi ^a  

^a Sichuan University   (China)

Author keywords

Alkene difunctionalization; Alkoxycarbonylation cyclization; Carbazates

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENE; ESTER; INDOLE DERIVATIVE; IRON; OXINDOLE; OXINDOLE 3 ACETATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLALKOXYCARBONYLATION; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84899413428     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.03.062     Document Type: Article

References (39)

1. T. Wu, X. Mu, and G.S. Liu Angew. Chem., Int. Ed. 50 2011 12578
2. M.-B. Zhou, C.-Y. Wang, R.-J. Song, Y. Liu, W.-T. Wei, and J.-H. Li Chem. Commun. 2013 10817
3. Y. Meng, L.-N. Guo, H. Wang, and X.-H. Duan Chem. Commun. 2013 7540
4. J. Xie, P. Xu, H. Li, Q. Xue, H. Jin, Y. Cheng, and C. Zhu Chem. Commun. 2013 5672
5. C.F. Rosewall, P.A. Sibbald, D.V. Liskin, and F.E. Michael J. Am. Chem. Soc. 131 2009 9488
6. B.A. Hopkins, and J.P. Wolfe Angew. Chem., Int. Ed. 51 2012 9886
7. N.R. Babij, and J.P. Wolfe Angew. Chem., Int. Ed. 52 2013 9247
8. S.M. So, L. Mui, H. Kim, and J. Chin Acc. Chem. Res. 45 2012 1345
9. F. Cardona, and A. Goti Nat. Chem. 1 2009 269
10. R.M. de Figueiredo Angew. Chem., Int. Ed. 48 2009 1190
11. P. Chávez, J. Kirsch, C.H. Hövelmann, J. Streuff, M. Martínez-Belmonte, E.C. Escudero-Adán, E. Martin, and K. Muñiz Chem. Sci. 3 2012 2375
12. Y.-B. Kang, and L.H. Gade J. Am. Chem. Soc. 133 2011 3658
13. V.A. Schmidt, and E.J. Alexanian Angew. Chem., Int. Ed. 49 2010 4491
14. Y. Li, D. Song, and V.M. Dong J. Am. Chem. Soc. 130 2008 2962
15. I. Ryu, and N. Sonoda Angew. Chem., Int. Ed. 35 1996 1050
16. I. Ryu Chem. Soc. Rev. 30 2001 16
17. A. Brennführer, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 48 2009 4114
18. R.N. Saicic, and S.Z. Zard Chem. Commun. 1996 1631
19. S. Takahashi, and T. Nakata J. Org. Chem. 67 2002 5739
20. B.M. Trost, J. Waser, and A. Meyer J. Am. Chem. Soc. 130 2008 16424
21. T. Taniguchi, Y. Sugiura, H. Zaimoku, and H. Ishibashi Angew. Chem., Int. Ed. 49 2010 10154
22. Y.-H. Su, Z. Wu, and S.-K. Tian Chem. Commun. 2013 6528
23. A.J.-L. Ayitou, and J. Sivaguru Chem. Commun. 2011 2568
24. D.C. Fabry, M. Stodulski, S. Hoerner, and T. Gulder Chem. - Eur. J. 18 2012 10834
25. X. Mu, T. Wu, H.-Y. Wang, Y.-L. Guo, and G. Liu J. Am. Chem. Soc. 134 2012 878
26. W.-T. Wei, M.-B. Zhou, J.-H. Fan, W. Liu, R.-J. Song, Y. Liu, M. Hu, P. Xie, and J.-H. Li Angew. Chem., Int. Ed. 52 2013 3638
27. H. Egami, R. Shimizu, S. Kawamura, and M. Sodeoka Angew. Chem., Int. Ed. 52 2013 4000
28. K. Matcha, R. Narayan, and A.P. Antonchick Angew. Chem., Int. Ed. 52 2013 7985
29. S.-L. Zhou, L.-N. Guo, H. Wang, and X.-H. Duan Chem. - Eur. J. 19 2013 12970
30. X.-H. Wei, Y.-M. Li, A.-X. Zhou, T.-T. Yang, and S.-D. Yang Org. Lett. 15 2013 4158
31. H. Wang, L.-N. Guo, and X.-H. Duan Org. Lett. 15 2013 5254
32. X. Li, X. Xu, P. Hu, X. Xiao, and C. Zhou J. Org. Chem. 78 2013 7343
33. W. Fu, F. Xu, Y. Fu, M. Zhu, J. Yu, C. Xu, and D. Zou J. Org. Chem. 78 2013 12202
34. One case of carboalkoxycarbonylation of alkene with large dosage of ethyl formate under high temperature sees: M.-B. Zhou, R.-J. Song, X.-H. Ouyang, Y. Liu, W.-T. Wei, G.-B. Deng, and J.-H. Li Chem. Sci. 4 2013 2690
35. Y.-L. Luo, Q.-S. Yu, L. Chrisey, and A. Brossi Heterocycles 31 1990 283
36. J.-C. Jaton, K. Roulin, K. Rose, F.M. Sirotnak, A. Lewenstein, G. Brunner, C.P. Fankhauser, and U. Burger J. Nat. Prod. 60 1997 356
37. During the preparation of this manuscript, a similar work by Li group had published X. Xu, Y. Tang, X. Li, G. Hong, M. Fang, and X. Du J. Org. Chem. 79 2014 446 We found this reaction independently, and we can't repeat Li's excellent yields (without ligands and methyl carbazate was fed in one batch) in our laboratory
38. P.A. Simakov, F.N. Martinez, J.H. Horner, and M. Newcomb J. Org. Chem. 63 1998 1226
39. M.L. Coote, C.J. Easton, and S.Z. Zard J. Org. Chem. 71 2006 4996