Ruthenium-catalyzed C-H activation/cyclization for the synthesis of phosphaisocoumarins

Journal of Organic Chemistry

Volumn 78, Issue 20, 2013, Pages 10209-10220

  Park, Youngchul ^a   Jeon, Incheol ^a   Shin, Seohyun ^a   Min, Jiae ^a   Lee, Phil Ho ^a  

^a Kangwon National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC CONDITION; DIARYLACETYLENES; ELECTRON-DONATING; ELECTRONIC EFFECTS; MECHANISTIC STUDIES; OXIDATIVE CYCLIZATION; PHOSPHONIC ACIDS; RATE-LIMITING STEPS;

CATALYSIS; HYDROCARBONS; RUTHENIUM;

CYCLIZATION;

ISOCOUMARIN DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; PHOSPHONIC ACID ESTER; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CYCLIZATION; DRUG SYNTHESIS; OXIDATION;

EID: 84886251219     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401608v     Document Type: Article

References (56)

1. Name Reactions in Heterocyclic Chemistry; Li, J.-J., Corey, E. J., Eds.; Wiley-Interscience: Hoboken, NJ, 2005.
2. Dillon, K. B.; Mathey, F.; Nixon, J. F. in Phosphorus: The Carbon Copy, John Wiley & Sons, Chichester, 1998.
3. Seto, H.; Kuzuyama, T. Nat. Prod. Rep. 1999, 16, 589
4. Li, X. S.; Zhang, D. W.; Pang, H.; Shen, F.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Org. Lett. 2005, 7, 4919
5. Peng, A.-Y.; Ding, Y.-X. Org. Lett. 2005, 7, 3299
6. Wei, T.; Ding, Y.-X. J. Org. Chem. 2006, 71, 8489
7. Li, B.; Zhou, B.; Lu, H.; Ma, L.; Peng, A.-Y. Eur. J. Med. Chem. 2010, 45, 1955
8. Ruda, G. F.; Wong, P. E.; Alibu, V. P.; Norval, S.; Read, K. D.; Barrett, M. P.; Gilbert, I. H. J. Med. Chem. 2010, 53, 6071
9. Chan, L. Y.; Kim, S.; Ryu, T.; Lee, P. H. Chem. Commun. 2013, 49, 4682
10. Chary, B. C.; Kim, S.; Park, Y.; Kim, J.; Lee, P. H. Org. Lett. 2013, 15, 2692
11. Seo, J.; Park, Y.; Jeon, I.; Ryu, T.; Park, S.; Lee, P. H. Org. Lett. 2013, 15, 3358
12. Ryu, T.; Kim, J.; Park, Y.; Kim, S.; Lee, P. H. Org. Lett. 2013, 15, 3986
13. Park, S.; Seo, B.; Shin, S.; Son, J.-Y.; Lee, P. H. Chem. Commun. 2013, 49, 8671
14. Mo, J.; Lim, S.; Ryu, T.; Kim, S.; Lee, P. H. RSC Adv. 2013, 10.1039/C3RA43764G
15. Park, Y.; Seo, J.; Park, S.; Yoo, E. J.; Lee, P. H. Chem. Eur. J. 2013, 10.1002/chem.201302652
16. Meng, X.; Kim, S. Org. Lett. 2013, 15, 1910
17. Chan, L. Y.; Cheong, L.; Kim, S. Org. Lett. 2013, 15, 2186
18. Chan, L. Y.; Meng, X.; Kim, S. J. Org. Chem. 2013, 78, 8826
19. Chary, B. C.; Kim, S. Org. Biomol. Chem. 2013, 10.1039/C3OB41548A
20. Chary, B. C.; Low, W. S.; Kim, S.; Kim, H.; Lee, P. H. Chem. Asian J. 2011, 6, 1970
21. Mo, J. T.; Kang, D.; Eom, D.; Kim, S. H.; Lee, P. H. Org. Lett. 2013, 15, 26
22. Kang, D.; Cho, J.; Lee, P. H. Chem. Commun. 2013, 10.1039/C3CC45874A
23. Peng, A.-Y.; Ding, Y.-X. J. Am. Chem. Soc. 2003, 125, 15006
24. Peng, A.-Y.; Ding, Y.-X. Org. Lett. 2004, 6, 1119
25. Peng, A.-Y.; Hao, F.; Li, B.; Wang, Z.; Du, Y. J. Org. Chem. 2008, 73, 9012
26. Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013
27. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev 2009, 38, 3242
28. Ackermann, L.; Vicente, R.; Kapdi, A. Angew. Chem., Int. Ed. 2009, 48, 9792
29. Thansandote, P.; Lautens, M. Chem. Eur. J. 2009, 15, 5874
30. Yoo, W.-J.; Li, C.-J. Top. Curr. Chem. 2010, 292, 281
31. Ackermann, L.; Potukuchi, H. K. Org. Biomol. Chem. 2010, 8, 4503
32. Daugulis, O. Top. Curr. Chem. 2010, 292, 57
33. Ackermann, L. Chem. Commun. 2010, 46, 4866
34. Fagnou, K. Top. Curr. Chem. 2010, 292, 35
35. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
36. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
37. Wencel-Delord, J.; Droege, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740
38. Dangel, B. D.; Johnson, J. A.; Sames, D. J. Am. Chem. Soc. 2001, 123, 8149
39. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560
40. Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931
41. Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932
42. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 16184
43. Wasa, M.; Yu, J. Q. J. Am. Chem. Soc. 2008, 130, 14058
44. Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411
45. Mei, T. S.; Wang, X.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 10806
46. Thansandote, P.; Lautens, M. Chem. Eur. J. 2009, 15, 5874
47. Neumann, J. J.; Rakshit, S.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 6892
48. Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217
49. Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203
50. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
51. Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362
52. Ackermann, L.; Pospech, J.; Graczyk, K.; Rauch, K. Org. Lett. 2012, 14, 930
53. Chinnagolla, R. K.; Jeganmohan, M. Chem. Commun. 2012, 48, 2030
54. Unoh, Y.; Hashimoto, Y.; Takeda, D.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2013, 15, 3258
55. Mio, M. J.; Kopel, L. C.; Braun, J. B.; Gadzikwa, T. L.; Hull, K. L.; Brisbois, R. G.; Markworth, C. J.; Grieco, P. A. Org. Lett. 2002, 4, 3199
56. Severin, R.; Reimer, J.; Doye, S. J. Org. Chem. 2010, 75, 3518