Additive-free decarboxylative coupling of cinnamic acid derivatives in water: Synthesis of allyl amines

Organic Letters

Volumn 17, Issue 5, 2015, Pages 1300-1303

  Park, Kyungho ^a   Lee, Sunwoo ^a  

^a Chonnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBON DIOXIDE; CINNAMIC ACID; CINNAMIC ACID DERIVATIVE; WATER;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMINES; CARBON DIOXIDE; CATALYSIS; CINNAMATES; MOLECULAR STRUCTURE; STEREOISOMERISM; WATER;

EID: 84924255366     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b00303     Document Type: Article

References (50)

1. Sheldon, R. Green Chem. 2000, 2, G1-G4
2. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2.
3. L. Hjeresen, D. Pure Appl. Chem. 2001, 73, 1237-1241
4. Gawande, M. B.; Bonifacio, V. D. B.; Luque, R.; Branco, P. S.; Varma, R. S. Chem. Soc. Rev. 2013, 42, 5522-5551
5. DeSimone, J. M. Science 2002, 297, 799-803
6. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275-3279
7. Hailes, H. C. Org. Process Res. Dev. 2006, 11, 114-120
8. Li, C.-J. Chem. Rev. 2005, 105, 3095-3166
9. Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772
10. Kitanosono, T.; Kobayashi, S. Adv. Synth. Catal. 2013, 355, 3095-3118
11. Kobayashi, S. Pure Appl. Chem. 2013, 85, 1089-1101
12. Simon, M.-O.; Li, C.-J. Chem. Soc. Rev. 2012, 41, 1415-1427
13. Pirrung, M. C.; Sarma, K. D. J. Am. Chem. Soc. 2003, 126, 444-445
14. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725-748
15. Du, W.; Lai, J.; Tian, L.; Xie, X.; She, X.; Tang, S. Chem. Commun. 2014, 50, 14017-14020
16. Guastavino, J. F.; Budén, M. E.; Rossi, R. A. J. Org. Chem. 2014, 79, 9104-9111
17. Leadbeater, N. E.; Marco, M. Angew. Chem., Int. Ed. 2003, 42, 1407-1409
18. Park, K.; Heo, Y.; Lee, S. Org. Lett. 2013, 15, 3322-3325
19. Sun, C.-L.; Shi, Z.-J. Chem. Rev. 2014, 114, 9219-9280
20. Zhao, J.; Zhao, Y.; Fu, H. Angew. Chem., Int. Ed. 2011, 50, 3769-3773
21. Usui, Y.; Sato, K.; Tanaka, M. Angew. Chem., Int. Ed. 2003, 42, 5623-5625
22. Xu, Q.-L.; Gao, H.; Yousufuddin, M.; Ess, D. H.; Kürti, L. J. Am. Chem. Soc. 2013, 135, 14048-14051
23. Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.; DeBoef, B. J. Am. Chem. Soc. 2011, 133, 19960-19965
24. Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689-1708
25. Petranyi, G.; Ryder, N.; Stutz, A. Science 1984, 224, 1239-1241
26. Kariya, S.; Isozaki, S.; Uchino, K.; Suzuki, T.; Narimatsu, S. Biol. Pharm. Bull. 1996, 19, 1511-1514
27. Casy, A. F.; Ganellin, C. R.; Mercer, A. D.; Upton, C. J. Pharm. Pharmacol. 1992, 44, 791-795
28. Kitahata, N.; Han, S.-Y.; Noji, N.; Saito, T.; Kobayashi, M.; Nakano, T.; Kuchitsu, K.; Shinozaki, K.; Yoshida, S.; Matsumoto, S.; Tsujimoto, M.; Asami, T. Biorg. Med. Chem. 2006, 14, 5555-5561
29. Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698
30. Goldberg, A. F. G.; Stoltz, B. M. Org. Lett. 2011, 13, 4474-4476
31. Klein, C. D. P.; Tabeteh, G. F.; Laguna, A. V.; Holzgrabe, U.; Mohr, K. Eur. J. Pharm. Sci. 2001, 14, 167-175
32. Gansäuer, A.; Behlendorf, M.; von Laufenberg, D.; Fleckhaus, A.; Kube, C.; Sadasivam, D. V.; Flowers, R. A. Angew. Chem., Int. Ed. 2012, 51, 4739-4742
33. Chen, Y. K.; Lurain, A. E.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 12225-12231
34. Sen, S. E.; Roach, S. L. Synthesis 1995, 1995, 756-758
35. Leitner, A.; Shu, C.; Hartwig, J. F. Org. Lett. 2005, 7, 1093-1096
36. Ohshima, T.; Miyamoto, Y.; Ipposhi, J.; Nakahara, Y.; Utsunomiya, M.; Mashima, K. J. Am. Chem. Soc. 2009, 131, 14317-14328
37. Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. Angew. Chem., Int. Ed. 2014, 53, 3688-3692
38. Nagano, T.; Kobayashi, S. J. Am. Chem. Soc. 2009, 131, 4200-4201
39. Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 15164-15165
40. Li, Y.; Zhang, X.-S.; Zhu, Q.-L.; Shi, Z.-J. Org. Lett. 2012, 14, 4498-4501
41. Xie, Y.; Hu, J.; Wang, Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613-20616
42. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169-6193
43. Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857-873
44. Lim, J.; Park, K.; Byeun, A.; Lee, S. Tetrahedron Lett. 2014, 55, 4875-4878
45. Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Adv. Synth. Catal. 2011, 353, 631-636
46. Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 592-595
47. Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2010, 39, 68-69
48. Das, J. P.; Roy, U. K.; Roy, S. Organometallics 2005, 24, 6136-6140
49. Petasis, N. A.; Boral, S. Tetrahedron Lett. 2001, 42, 539-542
50. Homsi, F.; Rousseau, G. J. Org. Chem. 1999, 64, 81-85