A general preparation of polyfunctional benzylic zinc organometallic compounds

Chemistry - An Asian Journal

Volumn 3, Issue 8-9, 2008, Pages 1678-1691

  Metzger, Albrecht ^a   Schade, Matthias A ^a   Manolikakes, Georg ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Insertion; Nickel; Organometallics; Zinc

Indexed keywords

EID: 54849411259     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800161     Document Type: Article

References (58)

1. a) P. Knochel, R. D. Singer, Chem. Rev. 1993, 93, 2117;
2. b) P. Knochel, N. Millot, A. Rodriguez, C. E. Tucker, Org. React. 2001, 58, 417;
3. c) P. Knochel, H. Leuser, L.-Z. Gong, S. Perrone, F. F. Kneisel in Handbook of Functionalized Organometallics (Ed.: P. Knochel), Wiley-VCH, 2005, chap. 7.
4. Zinc is a cheap metal: 1 kg costs 21.30€ (98%, <10 μm, Aldrich 2007).
5. a) A. H. Stoll, A. Krasovskiy, P. Knochel, Angew. Chem. 2006, 118, 621;
6. Angew. Chem. Int. Ed. 2006, 45, 606;
7. b) M. Yuguchi, M. Tokuda, K. Orito, J. Org. Chem. 2004, 69, 908;
8. c) C. Piazza, N. Millot, P. Knochel, J. Organomet. Chem. 2001, 624, 88;
9. d) J. X. Wang, Y. Fu, Y. L. Hu, Chin. Chem. Lett. 2002, 5, 405;
10. e) S. C. Berk, M. C. P. Yeh, N. Jeong, P. Knochel, Organometallics 1990, 9, 3053;
11. f) T. Harada, T. Kaneko, T. Fujiwara, A. Oku, J. Org. Chem. 1997, 62, 8966.
12. a) A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 118, 6186;
13. Angew. Chem. Int. Ed. 2006, 45, 6040;
14. b) N. Boudet, S. Sase, P. Sinha, C.-Y. Liu, A. Krasovskiy, P. Knochel, J. Am. Chem. Soc. 2007, 129, 12358;
15. D. Soorukram, N. Boudet, V. Malakhov, P. Knochel, Synthesis 2007, 3915.
16. A. Metzger, M. A. Schade, P. Knochel, Org. Lett. 2008, 10, 1107.
17. Activation: 5 mol% dibromoethane and 1 mol% TMSCl; see also the Experimental Section.
18. A. Krasovskiy, P. Knochel, Synthesis 2006, 890.
19. P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390.
20. E. Nakamura, S. Matsuzawa, Y. Horiguchi, I. Kuwajima, Tetrahedron Lett. 1986, 27, 5181.
21. a) Q. Mingxing, E. Negishi, Tetrahedron Lett. 2005, 46, 2927;
22. b) E. Metay; Q. Hu, E. Negishi, Org. Lett. 2006, 8, 5773;
23. Q. Hu, E. Negishi, Org. Lett. 2006, 8, 5773;
24. c) E. Negishi, M. Qian, F. Zeng, L. Anastasia, D. Babinski, Org. Lett. 2003, 5, 1597;
25. d) E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc. 1980, 102, 3298;
26. e) M. Kobayashi, E. Negishi, J. Org. Chem. 1980, 45, 5223;
27. f) E. Negishi, Acc. Chem. Res. 1982, 15, 340;
28. g) M. Qian, E. Negishi, Tetrahedron Lett. 2005, 46, 2927;
29. h) X. Zeng, F. Zeng, E. Negishi, Org. Lett. 2004, 6, 3245;
30. i) X. Zeng, M. Qian, Q. Hu, E. Negishi, Angew. Chem. 2004, 116, 2309;
31. Angew. Chem. Int. Ed. 2004, 43, 2259;
32. j) M. Qian, Z. Huang, E. Negishi, Org. Lett. 2004, 6, 1531.
33. a) J. Villieras, M. Rambaud, Synthesis 1982, 924;
34. b) J. Villieras, M. Rambaud, Org. Synth. 1988, 66, 220.
35. A. Garcia Martinez, H. Fernadez, D. Molero Vilchez, M. L. Lardon Guiterrez, L. R. Subramanian, Synlett 1993, 229.
36. E. Negishi, V. Bagheri, S. Chatterjee, L.-F. Luo, J. A. Miller, A. T. Stoll, Tetrahedron Lett. 1983, 24, 5181.
37. a) I. D. Rae, P. M. Simmonds, Aust. J. Chem. 1987, 40, 915;
38. b) A. R. de Lera, S. Aubourg, R. Suau, L. Castedo, Heterocycles 1987, 26, 675.
39. S. Berger, F. Langer, C. Lutz, P. Knochel, T. Mobley, C. K. Reddy, Angew. Chem. 1997, 109, 1603;
40. Angew. Chem. Int. Ed. Engl. 1997, 36, 1496.
41. a) P. D. Leeson, J. C. Emmett, V. P. Shah, G. A. Showell, R. Novelli, H. D. Prain, M. G. Benson, D. Ellis, N. J. Pearce, A. H. Underwood, J. Med. Chem. 1989, 32, 320;
42. b) J. S. Wai, M. S. Egbertson, L. S. Payne, T. E. Fisher, M. W. Embrey, L. O. Tran, J. Y. Melamed, H. M. Langford, J. P. Guare, Jr., L. Zhuang, V. E. Grey, J. P. Vacca, M. K. Holloway, A. M. Naylor-Olsen, D. J. Hazuda, P. J. Felock, A. L. Wolfe, K. A. Stillmock, W. A. Schleif, L. J. Gabryelski, S. D. Young, J. Med. Chem. 2000, 43, 4923.
43. For the alternative preparation of diaryl methanes, see: a) D. A. Barda, Z.-Q. Wang, T. C. Britton, S. S. Henry, G. E. Jagdmann, D. S. Coleman, M. P. Johnson, S. L. Andis, D. D. Schoepp, Bioorg. Med. Chem. Lett. 2004, 14, 3099;
44. b) Y.-Q. Long, X.-H. Jiang, R. Dayam, T. Sanchez, R. Shoemaker, S. Sei, N. Neamati, J. Med. Chem. 2004, 47, 2561;
45. c) X. Wu, A. K. Mahalingam, M. Alterman, Tetrahedron Lett. 2005, 46, 1501;
46. d) P. E. Gordon, A. J. Frey, Tetrahedron Lett. 2001, 42, 831;
47. e) N. L'Hermite, A. Giraud, O. Provot, J.-F. Peyrat, M. Alami, J.-D. Brion, Tetrahedron 2006, 62, 11 994.
48. M. A. Schade, A. Metzger, S. Hug, P. Knochel, Chem. Commun. 2008, DOI: 10.1039/B903072C.
49. a) A. Gavryushin, C. Kofink, G. Manolikakes, P. Knochel, Org. Lett. 2005, 7, 4871;
50. b) P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu, Angew. Chem. 2003, 115, 4438;
51. Angew. Chem. Int. Ed. 2003, 42, 4302.
52. a) J. W. Han, N. Tokunaga, T. Hayashi, Synlett 2002, 871;
53. b) E. Shirakawa, K. Yamasaki, T. Hiyama, Synthesis 1998, 1544;
54. c) J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222;
55. d) J. Terao, S. Nii, F. A. Chowdhury, A. Nakamura, N. Kambe, Adv. Synth. Catal. 2004, 346, 905.
56. a) E.-I. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821;
57. b) E.-I. Negishi, H. Matsushita, N. Okukado, Tetrahedron Lett. 1981, 22, 2715.
58. A. Krasovskiy, P. Knochel, Synthesis 2006, 890.