Selective Co/Ti cooperatively catalyzed biaryl couplings of aryl halides with aryl metal reagents

Organic Letters

Volumn 15, Issue 20, 2013, Pages 5342-5345

  Zeng, Jing ^a   Liu, Kun Ming ^a   Duan, Xin Fang ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84886245593     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402599f     Document Type: Article

References (54)

1. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
2. Hartwig, J. F. Organo-transition Metal Chemistry; University Science Books: Sausalito, CA, 2010.
3. Liu, W.; Cao, H.; Zhang, H.; Zhang, H.; Chung, K. H.; He, C.; Wang, H.; Kwong, F. Y.; Lei, A. J. Am. Chem. Soc. 2010, 132, 16737
4. Sun, C.-L.; Li, H.; Yu, D.-G.; Yu, M.; Zhou, X.; Lu, X.-Y.; Huang, K.; Zheng, S.-F.; Li, B.-J.; Shi, Z.-J. Nat. Chem 2010, 2, 1044
5. De, S.; Ghosh, S.; Bhunia, S.; Sheikh, J. A.; Bisai, A. Org. Lett. 2012, 14, 4466
6. Budén, M. E.; Guastavino, J. F.; Rossi, R. A. Org. Lett. 2013, 15, 1174
7. De, S.; Mishra, S.; Kakde, B. N.; Dey, D.; Bisai, A. J. Org. Chem. 2013, 78, 7823
8. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
9. Miyaura, N. Cross-Coupling Reactions. A Practical Guide; Springer: Berlin, 2002.
10. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
11. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217
12. Plietker, B. Iron Catalysis in Organic Chemistry: Reactions and Applications; Wiley-VCH: Weinheim, 2008.
13. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317
14. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500
15. Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 1364
16. Czaplik, W. M.; Mayer, M.; Cvengroš, J.; Jacobi von Wangelin, A. ChemSusChem 2009, 2, 396
17. Yorimitsu, H.; Oshima, K. Pure Appl. Chem. 2006, 78, 441
18. Gosmini, C.; Bégouin, J.-M.; Moncomble, A. Chem. Commun. 2008, 3221
19. Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435
20. Gosmini, C.; Moncomble, A. Isr. J. Chem. 2010, 50, 568
21. Avedissian, H.; Bérillon, L.; Cahiez, G.; Knochel, P. Tetrahedron Lett. 1998, 39, 6163
22. Kamachi, T.; Kuno, A.; Matsuno, C.; Okamoto, S. Tetrahedron Lett. 2004, 45, 4677
23. Affo, W.; Ohmiya, H.; Fujioka, T.; Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; Inamura, Y.; Mizuta, T.; Miyoshi, K. J. Am. Chem. Soc. 2006, 128, 8068
24. Tsuji, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2006, 128, 1886
25. Ohmiya, H.; Yorimitsu, H.; Oshima, K. Org. Lett. 2006, 8, 3093
26. Ohmiya, H.; Wakabayashi, K.; Yorimitsu, H.; Oshima, K. Tetrahedron 2006, 62, 2207
27. Cahiez, G.; Chaboche, C.; Duplais, C.; Moyeux, A. Org. Lett. 2009, 11, 277
28. Chen, Q.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 428
29. Nicolas, L.; Angibaud, P.; Stansfield, I.; Bonnet, P.; Meerpoel, L.; Reymond, S.; Cossy, J. Angew. Chem., Int. Ed. 2012, 51, 11101
30. Gilman, H.; Lichtenwalter, M. J. Am. Chem. Soc. 1939, 61, 957
31. Kharasch, M. S.; Fuchs, C. F. J. Am. Chem. Soc. 1941, 63, 2316
32. Morizur, J. P. Bull. Soc. Chim. Fr. 1964, 1331
33. Moncomble, A.; Le Floch, P.; Gosmini, C. Chem.-Eur. J. 2009, 15, 4770
34. Mayer, M.; Czaplik, W. M.; Jacobi von Wangelin, A. Synlett 2009, 2919
35. Korn, T. J.; Knochel, P. Angew. Chem., Int. Ed. 2005, 44, 2947
36. Korn, T.; Schade, M.; Schade, S.; Knochel, P. Org. Lett. 2006, 8, 725
37. Amatore, M.; Gosmini, C. Angew. Chem., Int. Ed. 2008, 47, 2089
38. Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949
39. Bégouin, J.-M.; Rivard, M.; Gosmini, C. Chem. Commun. 2010, 46, 5972
40. Kuzmina, O. M.; Steib, A. K.; Markiewicz, J. T.; Flubacher, D.; Knochel, P. Angew. Chem., Int. Ed. 2013, 52, 4945
41. Gülak, S.; Stepanek, O.; Malberg, J.; Rad, B. R.; Kotora, M.; Wolf, R.; Jacobi von Wangelin, A. Chem. Sci. 2013, 4, 776
42. Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 12, 31
43. Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer: Verlag, 1986.
44. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807
45. Marek, I. Titanium and Zirconium in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
46. Arai, M.; Nakamura, E. J. Org. Chem. 1991, 56, 5489
47. Bernardi, A.; Cavicchioli, M.; Marchionni, C.; Potenza, D.; Scolastico, C. J. Org. Chem. 1994, 59, 3690
48. Mahrwald, R. Tetrahedron 1995, 51, 9015
49. Hayashi, T.; Tokunaga, N.; Inoue, K. Org. Lett. 2004, 6, 305
50. Itoh, Y.; Houk, K. N.; Mikami, K. J. Org. Chem. 2006, 71, 8918
51. Mikami, K.; Murase, T.; Itoh, Y. J. Am. Chem. Soc. 2007, 129, 11686
52. Manolikakes, G.; Dastbaravardeh, N.; Knochel, P. Synlett 2007, 2077
53. Muramatsu, Y.; Kanehira, S.; Tanigawa, M.; Miyawaki, Y.; Harada, T. Bull. Chem. Soc. Jpn. 2010, 83, 19 and references cited therein
54. For papers on the cross-coupling reactions of halides bearing acidic protons: Manolikakes, G.; Dong, Z., M.Sc.; Mayr, H.; Li, J.; Knochel, P. Chem.-Eur. J. 2009, 15, 1324 and references cited therein