Palladium-catalyzed cross-coupling reaction of diazo compounds and vinyl boronic acids: An approach to 1,3-diene compounds

Journal of Organic Chemistry

Volumn 79, Issue 16, 2014, Pages 7711-7717

  Xia, Yamu ^a,b   Xia, Ying ^b   Liu, Zhen ^b   Zhang, Yan ^b   Wang, Jianbo ^b  

^a QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OLEFINS;

1 ,3-DIENES; BORONIC ACID; CARBENES; CROSS-COUPLINGS; DIAZO COMPOUNDS; MIGRATORY INSERTION; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS;

CATALYSIS;

1,3 DIENE; BORONIC ACID DERIVATIVE; NATURAL PRODUCT; PALLADIUM; UNCLASSIFIED DRUG; ALKENE; AZO COMPOUND; CARBENE; METHANE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKENES; AZO COMPOUNDS; BORONIC ACIDS; METHANE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; VINYL COMPOUNDS;

EID: 84906091525     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5012703     Document Type: Article

References (43)

1. Peters, L.; König, G. M.; Terlau, H.; Wright, A. D. J. Nat. Prod. 2002, 65, 1633
2. Wnuk, S. F.; Ro, B.-O.; Valdez, C. A.; Lewandowska, E.; Valdez, N. X.; Sacasa, P. R.; Yin, D. Y.; Zhang, J.; Borchardt, R. T.; Clercq, E. D. J. Med. Chem. 2002, 45, 2651
3. Begemann, P.; Christova-Georgieva, N. I.; Sangaiah, R.; Koc, H.; Zhang, D.; Golding, B. T.; Gold, A.; Swenberg, J. A. Chem. Res. Toxicol. 2004, 17, 929
4. Mandal, A. K.; Schneekloth, J. S., Jr.; Crews, C. M. Org. Lett. 2005, 7, 3645
5. Li, C.; La, M.-P.; Li, L.; Li, X.-B.; Tang, H.; Liu, B.-S.; Krohn, K.; Sun, P.; Yi, Y.-H.; Zhang, W. J. Nat. Prod. 2011, 74, 1658
6. Ponnapakam, A. P.; Liu, J.; Bhinge, K. N.; Drew, B. A.; Wang, T. L.; Antoon, J. W.; Nguyen, T. T.; Dupart, P. S.; Wang, Y.; Zhao, M.; Liu, Y. Y.; Foroozesh, M.; Beckman, B. S. Bioorg. Med. Chem. 2014, 22, 1412
7. Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2001, 123, 2895
8. Tobisch, A. Acc. Chem. Res. 2002, 35, 96
9. Ohmura, T.; Masuda, K.; Takase, I.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 16624
10. Jiménez, M. V.; Pérez-Torrente, J. J.; Bartolomé, M. I.; Vispe, E.; Lahoz, F. J.; Oro, L. A. Macromolecules 2009, 42, 8146
11. Kitamura, T.; Tanaka, N.; Mihashi, A.; Matsumoto, A. Macromolecules 2010, 43, 1800
12. Tanaka, N.; Sato, E.; Matsumoto, A. Macromolecules 2011, 44, 9125
13. Pham, H. V.; Paton, R. S.; Ross, A. G.; Danishefsky, S. J.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 2397
14. Parker, S. E.; Börgel, J.; Ritter, T. J. Am. Chem. Soc. 2014, 136, 4857
15. Luken, C.; Moberg, C. Org. Lett. 2008, 10, 2505
16. Lindhardt, A. T.; Mantel, M. L. H.; Skrydstrup, T. Angew. Chem., Int. Ed. 2008, 47, 2668
17. Negishi, E.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474
18. Ogata, K.; Murayama, H.; Sugasawa, J.; Suzuki, N.; Fukuzawa, S.-I. J. Am. Chem. Soc. 2009, 131, 3176
19. Huang, J.; Dong, Y.; Wang, X. X.; Luo, H. C. Chem. Commun. 2010, 46, 1035
20. Billard, F.; Robiette, R.; Pospíšil, J. J. Org. Chem. 2012, 77, 6358
21. Li, W.; Zhang, J. Org. Lett. 2014, 16, 162
22. Greenman, K. L.; Carter, D. S.; Van Vranken, D. L. Tetrahedron 2001, 57, 5219
23. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 1015
24. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486
25. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560
26. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586-2598
27. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
28. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024
29. Barluenga, J.; Moriel, P.; Valdés, C.; Aznar, F. Angew. Chem., Int. Ed. 2007, 46, 5587
30. Devine, S. K. J.; Van Vranken, D. L. Org. Lett. 2007, 9, 2047
31. Kudirka, R.; Devine, S. K. J.; Adams, C. S.; Van Vranken, D. L. Angew. Chem., Int. Ed. 2009, 48, 3677
32. Chen, Z.-S.; Duan, X.-H.; Zhou, P.-X.; Ali, S.; Luo, J.-Y.; Liang, Y.-M. Angew. Chem., Int. Ed. 2012, 51, 1370
33. Zhou, P.-X.; Zhou, Z.-Z.; Chen, Z.-S.; Ye, Y.-Y.; Zhao, L.-B.; Yang, Y.-F.; Xia, X.-F.; Luo, J.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 561
34. Yang, K.; Zhang, J.; Li, Y.; Cheng, B.; Zhao, L.; Zhai, H. Org. Lett. 2013, 15, 808
35. Zhou, P.-X.; Luo, J.-Y.; Zhao, L.-B.; Ye, Y.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 3254
36. Chen, S.; Wang, J. Chem. Commun. 2008, 4198
37. Xiao, Q.; Wang, B.; Tian, L.; Yang, Y.; Ma, J.; Zhang, Y.; Chen, S.; Wang, J. Angew. Chem., Int. Ed. 2013, 52, 9305
38. Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1566
39. DeAngelis, A.; Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2012, 134, 11035
40. Rossi, R.; Bellina, F.; Ciucci, D. J. Organomet. Chem. 1997, 542, 113
41. Rossi, R.; Bellina, F.; Ciucci, D.; Carpita, A.; Fanelli, C. Tetrahedron 1998, 54, 7595
42. Crist, R. M.; Reddy, P. V.; Borhan, B. Tetrahedron Lett. 2001, 42, 619
43. Lim, C. H.; Kim, S. H.; Park, K. H.; Lee, J.; Kim, J. N. Tetrahedron Lett. 2013, 54, 387