Pd(0)-catalyzed alkenylation and allylic dearomatization reactions between nucleophile-bearing indoles and propargyl carbonate

Organic Letters

Volumn 16, Issue 15, 2014, Pages 3919-3921

  Gao, Run Duo ^a   Liu, Chuan ^a   Dai, Li Xin ^a   Zhang, Wei ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBONIC ACID DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM; SPIRO COMPOUND;

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

ALKYNES; CARBONATES; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; PALLADIUM; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84905395943     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501704q     Document Type: Article

References (52)

1. Takano, S.; Ogasawara, K. Alkaloids 1989, 36, 225
2. Dewick, P. M. Medicinal Natural Products: A Biosynthetic Approach, 2 nd ed.; Wiley: New York, 2002.
3. Fattorusso, E.; Scafati, O. T. Modern Alkaloids; Wiley-VCH: Weinheim, 2008.
4. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068
5. Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 12662
6. Bocchi, V.; Casnati, G.; Marchelli, R. Tetrahedron. 1978, 34, 929
7. Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 5917
8. Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482
9. Bajtos, B.; Yu, M.; Zhao, H.; Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631
10. Zhang, G.; Catalano, V. J.; Zhang, L. J. Am. Chem. Soc. 2007, 129, 11358
11. Gioia, C.; Hauville, A.; Bernardi, L.; Fini, F.; Ricci, A. Angew. Chem., Int. Ed. 2008, 47, 9236
12. Barluenga, J.; Tudela, E.; Ballesteros, A.; Tomás, M. J. Am. Chem. Soc. 2009, 131, 2096
13. Jones, S. B.; Simmons, B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 13606
14. Zheng, C.; Lu, Y.; Zhang, J.; Chen, X.; Chai, Z.; Ma, W.; Zhao, G. Chem.-Eur. J. 2010, 16, 5853
15. Han, B.; Xiao, Y.-C.; Yao, Y.; Chen, Y.-C. Angew. Chem., Int. Ed. 2010, 49, 10189
16. Lian, Y.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 440
17. Repka, L. M.; Ni, J.; Reisman, S. E. J. Am. Chem. Soc. 2010, 132, 14418
18. Jones, S. B.; Simmons, B.; Mastracchio, A.; MacMillan, D. W. C. Nature. 2011, 475, 183
19. Lozano, O.; Blessley, G.; del Campo, T. M.; Thompson, A. L.; Giuffredi, G. T.; Bettati, M.; Walker, M.; Borman, R.; Gouverneur, V. Angew. Chem., Int. Ed. 2011, 50, 8105
20. Cai, Q.; You, S.-L. Org. Lett. 2012, 14, 3040
21. Yin, Q.; You, S.-L. Org. Lett. 2013, 15, 4266
22. Liu, C.; Zhang, W.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 4525
23. Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802
24. Xiong, H.; Xu, H.; Liao, S.; Xie, Z.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 7851
25. Yin, Q.; You, S.-L. Org. Lett. 2014, 16, 2426
26. Han, L.; Liu, C.; Zhang, W.; Shi, X.-X.; You, S.-L. Chem. Commun. 2014, 50, 1231
27. Cai, Q.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2011, 50, 8665
28. Cera, G.; Chiarucci, M.; Mazzanti, A.; Mancinelli, M.; Bandini, M. Org. Lett. 2012, 14, 1350
29. Wu, K.-J.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 3772
30. Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592
31. Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314
32. Kagawa, N.; Malerich, J. P.; Rawal, V. H. Org. Lett. 2008, 10, 2381
33. Wu, Q.-F.; He, H.; Liu, W.-B.; You, S.-L. J. Am. Chem. Soc. 2010, 132, 11418
34. Wu, Q.-F.; Zheng, C.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 1680
35. Zhuo, C.-X.; Wu, Q.-F.; Zhao, Q.; Xu, Q.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 8169
36. Xu, Q.-L.; Dai, L.-X.; You, S.-L. Chem. Sci. 2013, 4, 97
37. Zhang, X.; Yang, Z.-P.; Liu, C.; You, S.-L. Chem. Sci. 2013, 4, 3239
38. Liu, Y.; Du, H. Org. Lett. 2013, 15, 740
39. Chen, J.; Cook, M. J. Org. Lett. 2013, 15, 1088
40. Montgomery, T. D.; Zhu, Y.; Kagawa, N.; Rawal, V. H. Org. Lett. 2013, 15, 1140
41. Zhang, X.; Liu, W.-B.; Wu, Q.-F.; You, S.-L. Org. Lett. 2013, 15, 3746
42. Kaiser, T. M.; Yang, J. J. Eur. J. Org. Chem. 2013, 3983
43. Zhang, X.; Han, L.; You, S.-L. Chem. Sci. 2014, 5, 1059
44. Nemoto, T.; Zhao, Z.; Yokosaka, T.; Suzuki, Y.; Wu, R.; Hamada, Y. Angew. Chem., Int. Ed. 2013, 52, 2217
45. Iwata, A.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Chem. Commun. 2014, 50, 298
46. During revision of this manuscript, an elegant report on Pd-catalyzed cascade reactions of tryptamine derivatives and propargyl carbonate appeared: Montgomery, T. D.; Nibbs, A. E.; Zhu, Y.; Rawal, V. H. Org. Lett. 2014, 16, 3480
47. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; John Wiley & Sons, Ltd.: Chichester, 2004.
48. Yoshida, M. Heterocycles 2013, 87, 1835
49. Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196
50. Dominczak, N.; Damez, C.; Rhers, B.; Labrosse, J.-R.; Lhoste, P.; Kryczka, B.; Sinou, D. Tetrahedron 2005, 61, 2589
51. Millán, A.; álvarez de Cienfuegos, L.; Martín- Lasanta, A.; Campaña, A. G.; Cuerva, J. M. Adv. Synth. Catal. 2011, 353, 73
52. Yoshida, M.; Sugimura, C. Tetrahedron Lett. 2013, 54, 2082