Triarylphosphines as Aryl Donors for Pd(II)-Catalyzed Aromatic Coupling of Oxabenzonorbornadienes

Organic Letters

Volumn 17, Issue 18, 2015, Pages 4628-4631

  Zhou, Hui ^a,c   Li, Jixing ^a,c   Yang, Huameng ^a   Xia, Chungu ^a   Jiang, Gaoxi ^a,b  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SUZHOU INSTITUTE OF NANO TECH AND NANO BIONICS   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84941890254     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02366     Document Type: Article

References (46)

1. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998.
2. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals, 2 nd ed.; Wiley-VCH: Weinheim, 2004.
3. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651 10.1021/cr0505268
4. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417 10.1021/cr100327p
5. Halford, B. Chem. Eng. News 2010, 88 (41) 7 10.1021/cen-v088n041.p007
6. Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863 10.1021/cr00094a007
7. Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937 10.1021/ar800108z
8. Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023 10.1021/cr100105a
9. Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535 10.1021/ar000253x
10. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035 10.1002/adsc.200404087
11. Ye, L.-W.; Zhou, J.; Tang, Y. Chem. Soc. Rev. 2008, 37, 1140 10.1039/b717758e
12. Cowen, B. J.; Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102 10.1039/b816700c
13. Marinetti, A.; Voituriez, A. Synlett 2010, 2010, 174 10.1055/s-0029-1219157
14. Kolesinska, B. Cent. Eur. J. Chem. 2010, 8, 1147 10.2478/s11532-010-0114-z
15. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications; Börner, A., Ed.; Wiley-VCH: Weinheim, 2008.
16. Privileged Chiral Ligands and Catalysts; Zhou, Q.-L., Ed.; Wiley-VCH: Weinheim, 2011.
17. van Leeuwen, P. W. N. M.; Kamer, P. C. J.; Claver, C.; Pàmies, O.; Diéguez, M. Chem. Rev. 2011, 111, 2077 10.1021/cr1002497
18. Fernández-Pérez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A. Chem. Rev. 2011, 111, 2119 10.1021/cr100244e
19. Comprehensive Handbook of Chemical Bond Energies; Luo, Y.-R., Ed.; CRC Press: Boca Raton, FL, 2007.
20. Kikukawa, K.; Yamane, T.; Takagi, M.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1972, 695 10.1039/c39720000695
21. Kikukawa, K.; Takagi, M.; Matsuda, T. Bull. Chem. Soc. Jpn. 1979, 52, 1493 10.1246/bcsj.52.1493
22. Fahey, D. R.; Mahan, J. E. J. Am. Chem. Soc. 1976, 98, 4499 10.1021/ja00431a028
23. Chakravarty, A. R.; Cotton, F. A. Inorg. Chem. 1985, 24, 3584 10.1021/ic00216a021
24. Dubois, R. A.; Garrou, P. E. Organometallics 1986, 5, 466 10.1021/om00134a013
25. Heyn, R. H.; Görbitz, C. H. Organometallics 2002, 21, 2781 10.1021/om0200712
26. Kabir, S. E.; Ahmed, F.; Ghosh, S.; Hassan, M. R.; Islam, M. S.; Sharmin, A.; Tocher, D. A.; Haworth, D. T.; Lindeman, S. V.; Siddiquee, T. A.; Bennett, D. W.; Hardcastle, K. I. J. Organomet. Chem. 2008, 693, 2657 10.1016/j.jorganchem.2008.05.001
27. Liniger, M.; Gschwend, B.; Neuburger, M.; Schaffner, S.; Pfaltz, A. Organometallics 2010, 29, 5953 10.1021/om1007874
28. Shaw, B. K.; Patrick, B. O.; Fryzuk, M. D. Organometallics 2012, 31, 783 10.1021/om201233e
29. Kwong, F. Y.; Chan, K. S. Organometallics 2000, 19, 2058 10.1021/om9909338
30. Kwong, F. Y.; Lai, C. W.; Yu, M.; Tian, Y.; Chan, K. S. Tetrahedron 2003, 59, 10295 10.1016/j.tet.2003.10.061
31. Kwong, F. Y.; Chan, K. S. Chem. Commun. 2000, 1069 10.1039/b002656p
32. Cao, J.; Huang, X.; Wu, L. Chem. Commun. 2013, 49, 7747 10.1039/c3cc43640c
33. Baba, K.; Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11892 10.1002/anie.201307115
34. Baba, K.; Tobisu, M.; Chatani, N. Org. Lett. 2015, 17, 70 10.1021/ol503252t
35. Inoue, A.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 1484 10.1021/ja026758v
36. Lautens, M.; Renaud, J.-R.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804 10.1021/ja993427i
37. Lautens, M.; Hiebert, S.; Renaud, J.-R. J. Am. Chem. Soc. 2001, 123, 6834 10.1021/ja010498k
38. Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett. 2002, 4, 1311 10.1021/ol0256062
39. Wallow, T. I.; Goodson, F. E.; Novak, B. M. Organometallics 1996, 15, 3708 10.1021/om9602567
40. Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203 10.1021/ja105366u
41. Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576 10.1021/ja00138a012
42. Goodson, F. E.; Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1997, 119, 12441 10.1021/ja972554g
43. Nishimura, T.; Kawamoto, T.; Sasaki, K.; Tsurumaki, E.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 1492 10.1021/ja068488c
44. Caple, R.; Chen, G. M. S.; Nelson, J. D. J. Org. Chem. 1971, 36, 2874 10.1021/jo00818a032
45. Lautens, M.; Gajda, C. Tetrahedron Lett. 1993, 34, 4591 10.1016/S0040-4039(00)60632-9
46. Zhang, T.-K.; Mo, D.-L.; Dai, L.-X.; Hou, X.-L. Org. Lett. 2008, 10, 5337 10.1021/ol801946e