Mild and catalyst-free petasis/decarboxylative domino reaction: Chemoselective synthesis of N -benzyl propargylamines

Journal of Organic Chemistry

Volumn 79, Issue 23, 2014, Pages 11812-11818

  Feng, Huangdi ^a   Jia, Huihui ^a   Sun, Zhihua ^a  

^a SHANGHAI UNIVERSITY OF ENGINEERING SCIENCE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; FUNCTIONAL GROUPS; REACTION KINETICS;

CHEMOSELECTIVE; DECARBOXYLATIVE COUPLINGS; DOMINO REACTIONS; FORMALDEHYDE SOLUTIONS; FUNCTIONALIZED COMPOUNDS; IN-SITU FORMATIONS; MULTI-COMPONENT DOMINO REACTION; PROPARGYLAMINES;

SYNTHESIS (CHEMICAL);

ACID; BENZYL DERIVATIVE; BORONIC ACID DERIVATIVE; FORMALDEHYDE; N BENZYL PROPARGYLAMINE; PROPIOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMOSENSITIVITY; CONTROLLED STUDY; DECARBOXYLATION; DECARBOXYLATIVE DOMINO REACTION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ONE POT SYNTHESIS; PETASIS REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME;

EID: 84916232250     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502349a     Document Type: Article

References (57)

1. Merkul, E.; Boersch, C.; Frank, W.; Muller, T. J. J. Org. Lett. 2009, 11, 2269
2. Yamamoto, Y.; Hayashi, H.; Saigoku, T.; Nishiyama, H. J. Am. Chem. Soc. 2005, 127, 10804
3. Campbell, M. J.; Toste, F. D. Chem. Sci. 2011, 2, 1369
4. Chen, J. S.; Properzi, R.; Uccello, D. P.; Young, J. A.; Dushin, R. G.; Starr, J. T. Org. Lett. 2014, 16, 4146
5. Ermolatev, D. S.; Bariwal, J. B.; Steenackers, H. P. L.; De Keersmaecker, S. C. J.; Van der Eycken, E. V. Angew. Chem., Int. Ed. 2010, 49, 9465
6. Bhonde, V. R.; Looper, R. E. J. Am. Chem. Soc. 2011, 133, 20172
7. Robles-Machin, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71, 5023
8. Yan, B.; Liu, Y. Org. Lett. 2007, 9, 4323
9. Liu, J. X.; Zhang, Y. D.; Li, G. S.; Roschangar, F.; Farina, V.; Senanayake, C. H.; Lu, B. Z. Adv. Synth. Catal. 2010, 352, 2667
10. Gainer, M. J.; Bennett, N. R.; Takahashi, Y.; Looper, R. E. Angew. Chem., Int. Ed. 2011, 50, 684
11. Pereshivko, O. P.; Peshkov, V. A.; Peshkov, A. A.; Jacobs, J.; Van Meervelt, L.; Van der Eycken, E. V. Org. Biomol. Chem. 2014, 12, 1741
12. M. Bhandari, R.; Yousufuddin, M.; Lovely, C. J. Org. Lett. 2011, 13, 1382
13. Ohta, Y.; Kubota, Y.; Watabe, T.; Chiba, H.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2009, 74, 6299
14. Xia, Y. Y.; Chen, L. Y.; Lv, S.; Sun, Z. H.; Wang, B. J. Org. Chem. 2014, 79, 9818
15. Nguyen, H. H.; Palazzo, T. A.; Kurth, M. J. Org. Lett. 2013, 15, 4492
16. Donald, J. R.; Martin, S. F. Org. Lett. 2011, 13, 852
17. Donald, J. R.; Wood, R. R.; Martin, S. F. ACS Comb. Sci. 2012, 14, 135
18. Buysse, K.; Farard, J.; Nikolaou, A.; Van derheyden, P.; Vauquelin, G.; Pedersen, D. S.; Tourwe, D.; Ballet, S. Org. Lett. 2011, 13, 6468
19. Mont, N.; Mehta, V. P.; Appukkuttan, P.; Beryozkina, T.; Toppet, S.; Van Hecke, K.; Van Meervelt, L.; Voet, A.; DeMaeyer, M.; Van der Eycken, E. V. J. Org. Chem. 2008, 73, 7509
20. Yu, P. H.; Bruce, A. D.; Boulton, A. A. J. Med. Chem. 1992, 35, 3705
21. Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790
22. Yoo, W. J.; Zhao, L.; Li, C. J. Aldrichimica Acta 2011, 44, 43
23. Seidel, D. Org. Chem. Front. 2014, 1, 426
24. Rodriguez, N.; Gooßen, L. J. Chem. Soc. Rev. 2011, 40, 5030
25. Weaver, J. D.; Recio, A., III.; Grenning, A. J.; Tung, J. A. Chem. Rev. 2011, 111, 1846
26. Park, K.; Lee, S. RSC Adv. 2013, 3, 14165
27. Dzik, W. I.; Lange, P. P.; Gooßen, L. J. Chem. Sci. 2012, 3, 2671
28. Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250
29. Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323
30. Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
31. Streuff, J.; White, D.; Virgil, S.; Stoltz, B. Nat. Chem. 2010, 2, 192
32. Park, A.; Park, K.; Kim, Y.; Lee, S. Org. Lett. 2011, 13, 944
33. Gooßen, L. J.; Zimmermann, B.; Knauber, T. Angew. Chem., Int. Ed. 2008, 47, 7103
34. Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330
35. Feng, Y. S.; Xu, Z. Q.; Mao, L.; Zhang, F. F.; Xu, H. J. Org. Lett. 2013, 15, 1472
36. Bi, H. P.; Zhao, L.; Liang, Y. M.; Li, C. J. Angew. Chem, Int. Ed. 2009, 48, 792
37. Bi, H. P.; Teng, Q.; Guan, M.; Chen, W. W.; Liang, Y. M.; Yao, X.; Li, C. J. J. Org. Chem. 2010, 75, 783
38. Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 1798
39. Feng, H. D.; Ermolatev, D. S.; Song, G. H.; Van der Eycken, E. V. J. Org. Chem. 2011, 76, 7608
40. Feng, H. D.; Ermolatev, D. S.; Song, G. H.; Van der Eycken, E. V. Org. Lett. 2012, 14, 1942
41. Feng, H. D.; Ermolatev, D. S.; Song, G. H.; Van der Eycken, E. V. J. Org. Chem. 2012, 77, 5149
42. Ermolatev, D. S.; Feng, H. D.; Song, G. H.; Van der Eycken, E. V. Eur. J. Org. Chem. 2014, 5346
43. Lim, J.; Park, K.; Byeun, A.; Lee, S. Tetrahedron Lett. 2014, 55, 4875
44. Park, K.; Heo, Y.; Lee, S. Org. Lett. 2013, 15, 3322
45. Giles, R. L.; Sullivan, J. D.; Steiner, A. M.; Looper, R. E. Angew. Chem, Int. Ed. 2009, 48, 3116
46. Feng, H. D.; Ermolatev, D. S.; Song, G. H.; Van der Eycken, E. V. Adv. Synth. Catal. 2012, 354, 505
47. Palani, T.; Park, K.; Kumar, M. R.; Jung, H. M.; Lee, S. Eur. J. Org. Chem. 2014, 26
48. Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583
49. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445
50. Morin, M. S. T.; Lu, Y.; Black, D. A.; Arndtsen, B. A. J. Org. Chem. 2012, 77, 2013
51. Muncipinto, G.; Moquist, P. N.; Schreiber, S. L.; Schaus, S. E. Angew. Chem., Int. Ed. 2011, 50, 8172
52. Frauenlob, R.; García, C.; Bradshaw, G. A.; Burke, H. M.; Bergin, E. J. Org. Chem. 2012, 77, 4445
53. Wang, J. Y.; Shen, Q. Y.; Li, P. Z.; Peng, Y. Q.; Song, G. H. Org. Biomol. Chem. 2014, 12, 5597
54. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169
55. Wang, J. Y.; Li, P. Z.; Shen, Q. Y.; Song, G. H. Tetrahedron Lett. 2014, 55, 3888
56. Eschweiler, W. Ber. 1905, 38, 880
57. Gibson, H. W. Chem. Rev. 1969, 69, 673