Palladium-catalyzed oxidative coupling of aromatic primary amines and alkenes under molecular oxygen: Stereoselective assembly of (Z)-enamines

Journal of Organic Chemistry

Volumn 78, Issue 22, 2013, Pages 11155-11162

  Ji, Xiaochen ^a   Huang, Huawen ^a   Wu, Wanqing ^a   Li, Xianwei ^a   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC PRIMARY AMINES; ENAMINES; MEDICINAL CHEMISTRY; MILD REACTION CONDITIONS; OXIDATIVE COUPLINGS; PALLADIUM-CATALYZED; STEREO-SELECTIVE;

ALKENYLATION; AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; FUNCTIONAL GROUPS; HYDROCARBONS; PALLADIUM; STEREOSELECTIVITY;

AMINES;

ALKENE; AROMATIC AMINE; ENAMINE; FUNCTIONAL GROUP; PALLADIUM;

ARTICLE; ATOMIC ABSORPTION SPECTROMETRY; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL ANALYSIS; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; CROSS COUPLING REACTION; CYCLIZATION; ELECTROPHILICITY; NUCLEOPHILICITY; OXIDATIVE COUPLING; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; STEREOCHEMISTRY;

EID: 84887923838     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402117r     Document Type: Article

References (60)

1. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
2. Shi, W.; Liu, C.; Lei, A. Chem. Soc. Rev. 2011, 40, 2761
3. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
4. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540
5. Li, C.-J. Acc. Res. Chem. 2009, 42, 335
6. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
7. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318
8. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301
9. Piera, J.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2008, 47, 3506
10. Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433
11. Toh, K. K.; Wang, Y.-F.; Jian, Ng, E. P.; Chiba, S. J. Am. Chem. Soc. 2011, 133, 13942
12. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
13. Ke, J.; He, C.; Liu, H.; Li, M.; Lei, A. Chem. Commun. 2013, 49, 7549
14. Zhao, M.; Wang, F.; Li, X. Org. Lett. 2012, 14, 1412
15. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
16. Neumann, J. J.; Suri, M.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7790
17. Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2009, 48, 8078
18. Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230
19. Guan, Z.-H.; Li, L.; Ren, Z.-H.; Li, J.; Zhao, M.-N. Green Chem. 2011, 13, 1664
20. Guan, Z.-H.; Yan, Z.-Y.; Ren, Z.-H.; Liua, X.-Y.; Liang, Y.-M. Chem. Commun. 2010, 46, 2823
21. Burk, M. J. Acc. Chem. Res. 2000, 33, 363
22. Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103
23. Sibi, M. P.; Asano, Y. J. Am. Chem. Soc. 2001, 123, 9708
24. Xiao, D.; Zhang, Z.; Zhang, X. Org. Lett. 1999, 1, 1679
25. Zhou, Y.-G.; Yang, P.-Y.; Han, X.-W. J. Org. Chem. 2005, 70, 1679
26. Panda, N.; Mothkuri, R. J. Org. Chem. 2012, 77, 9407
27. Ueno, S.; Shimizu, R.; Kuwano, R. Angew. Chem., Int. Ed. 2009, 48, 4543
28. Bolshan, Y.; Batey, R. A. Angew. Chem., Int. Ed. 2008, 47, 2109
29. Gooβen, L. J.; Salih, K. S. M.; Blanchot, M. Angew. Chem., Int. Ed. 2008, 47, 8492
30. Nicolaou, K. C.; Mathison, C. J. N. Angew. Chem., Int. Ed. 2005, 44, 5992
31. Gooβen, L. J.; Rauhaus, J. E.; Deng, G. Angew. Chem., Int. Ed. 2005, 44, 4042
32. Lin, S.; Yang, Z.-Q.; Kwok, B. H. B.; Koldobskiy, M.; Crews, C. M.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 6347
33. Shen, R.; Lin, C. T.; Bowman, E. J.; Bowman, B. J.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 7889
34. Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955
35. Cesati, R. R.; Dwyer, G.; Jones, R. C.; Hayes, M. P.; Yalamanchili, P.; Casebier, D. S. Org. Lett. 2007, 9, 5617
36. Klapars, A.; Campos, K. R.; Chen, C.-y.; Volante, R. P. Org. Lett. 2005, 7, 1185
37. Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973
38. Sun, C.; Camp, J. E.; Weinreb, S. M. Org. Lett. 2006, 8, 1779
39. Wang, L.; Liu, C.; Bai, R.; Pana, Y.; Lei, A. Chem. Commun. 2013, 49, 7923
40. Compared with the hydroamination of alkynes, the direct oxidative cross-coupling of amines and alkenes would be more cost effective. For example, the approximate price of methyl propiolate (per mole, Sigma-Aldrich): 640; methyl acrylate (per mole, Sigma-Aldrich): 24. For reference, see: Kotov, V.; Scarborough, C. C.; Stahl, S. S. Inorg. Chem. 2007, 46, 1910
41. Lee, J. M.; Ahn, D.-S.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006, 128, 12954
42. Timokhin, V. I.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 17888
43. Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868
44. Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 1242
45. Panda, N.; Jena, A. K.; Raghavender, M. ACS Catal. 2012, 2, 539
46. Obora, Y.; Shimizu, Y.; Ishii, Y. Org. Lett. 2009, 11, 5058
47. Mizuta, Y.; Yasuda, K.; Obora, Y. J. Org. Chem. 2013, 78, 6332
48. Bozell, J. J.; Hegedus, L. S. J. Org. Chem. 1981, 46, 2561
49. Ji, X.; Huang, H.; Wu, W.; Jiang, H. J. Am. Chem. Soc. 2013, 135, 5286
50. Ji, X.; Huang, H.; Li, Y.; Chen, H.; Jiang, H. Angew. Chem., Int. Ed. 2012, 51, 7292
51. Wu, W.; Jiang, H. Acc. Res. Chem. 2012, 45, 1736
52. Jiang, H.; Ji, X.; Li, Y.; Chen, Z.; Wang, A. Org. Biomol. Chem. 2011, 9, 5358
53. Thorwirth, R.; Stolle, A. Synlett 2011, 15, 2200
54. Matsumoto, S.; Mori, T.; Akazome, M. Synthesis 2010, 21, 3615
55. Yamazaki, K.; Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68, 6011
56. Toyota, M.; Fukumoto, K. Heterocycles 1990, 31, 1431
57. Fulloon, B. E.; Wentrup, C. Aust. J. Chem. 2009, 62, 115
58. Luzung, M. R.; Lewis, C. A.; Baran, P. S. Angew. Chem., Int. Ed. 2009, 48, 7025
59. Linton, E. C.; Kozlowski, M. C. J. Am. Chem. Soc. 2008, 130, 16162
60. Ludwig, J.; Bovens, S.; Brauch, C.; Elfringhoff, A. S.; Lehr, M. J. Med. Chem. 2006, 49, 2611