Cobalt-catalyzed benzylzincation of alkynes

Chemistry - A European Journal

Volumn 16, Issue 26, 2010, Pages 7688-7691

  Murakami, Kei ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alkenes; Benzylation; Carbometalation; Cobalt; Zinc

Indexed keywords

ARYLACETYLENES; BENZYLATION; CARBOMETALATION; COBALT SALTS; ESTROGEN RECEPTOR; STEREOSELECTIVE SYNTHESIS;

ACETYLENE; OLEFINS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL); ZINC;

COBALT;

EID: 77954298301     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001061     Document Type: Article

References (59)

1. a) M. H. Gezginci, B. N. Timmermann, Tetrahedron Lett. 2001, 42, 6083;
2. b) G. D. Brown, H.-F. Wong, Tetrahedron 2004, 60, 5439;
3. c) R. S. Ward, A. Pelter, M. I. Edwards, J. Gilmore, Tetrahedron 1996, 52, 12799;
4. d) T. Takeya, S. Yamaki, T. Itoh, H. Hosogai, S. Tobinaga, Chem. Pharm. Bull. 1998, 44, 909;
5. e) P. Sellès, Org. Lett. 2005, 7, 605.
6. M. J. Meegan, R. B. Hughes, D. G. Lloyd, D. C. Williams, D. M. Zisterer, J. Med. Chem. 2001, 44, 1072.
7. Recent reviews for cobalt-catalyzed reactions, see: a) H. Yorimitsu, K. Oshima, Pure Appl. Chem. 2006, 78, 441;
8. b) H. Shinokubo, K. Oshima, Eur. J. Org. Chem. 2004, 2081;
9. c) K. Oshima, Bull. Chem. Soc. Jpn. 2008, 81, 1;
10. d) C. Gosmini, J.-M. Bégouin, A. Moncomble, Chem. Commun. 2008, 3221;
11. e) A. Rudolph, M. Lautens, Angew. Chem. 2009, 121, 2694;
12. Angew. Chem. Int. Ed. 2009, 48, 2656;
13. f) M. Jeganmohan, C.-H. Cheng, Chem. Eur. J. 2008, 14, 10876;
14. g) W. Hess, J. Treutwein, G. Hilt, Synthesis 2008, 3537;
15. h) G. Cahiez, A. Moyeux, Chem. Rev. 2010, 110, 1435.
16. Recent reviews for carbometalation reactions, see: a) P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, New York, 1991, pp. 865-911;
17. b) I. Marek, J.-F. Normant in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 271 - 337;
18. c) E. Negishi, Z. Huang, G. Wang, S. Mohan, C. Wang, H. Hattori, Acc. Chem. Res. 2008, 41, 1474;
19. d) A. B. Flynn, W. W. Ogilvie, Chem. Rev. 2007, 107, 4698;
20. e) A. G. Fallis, P. Forgione, Tetrahedron 2001, 57, 5899;
21. f) K. Itami, J. Yoshida in The Chemistry of Organomagnesium Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, New York, 2008, Chapter 18.
22. There are few reports on transition metal-catalyzed benzylzincation of limited alkynes. Ynamide: a) B. Gourdet, M. E. Rudkin, C. A. Watts, H. W. Lam, J. Org. Chem. 2009, 74, 7849;
23. b) B. Gourdet, H. W. Lam, J. Am. Chem. Soc. 2009, 131, 3802; 1-alkynyl sulfoxides:
24. c) N. Maezaki, H. Sawamoto, R. Yoshigami, T. Suzuki, T. Tanaka, Org. Lett. 2003, 5, 1345.
25. For examples of benzylmetalation of alkynes, see: a) J. G. Duboudin, B. Jousseaume, A. Saux, J. Organomet. Chem. 1979, 168, 1;
26. b) H. Nishiyama, M. Sasaki, K. Itoh, Chem. Lett. 1981, 10, 905;
27. c) Y. Ishino, K. Wakamoto, T. Hirashima, Chem. Lett. 1984, 13, 765;
28. d) N. Fujiwara, Y. Yamamoto, J. Org. Chem. 1999, 64, 4095;
29. e) M. P. Jennings, K. B. Sawant, Eur. J. Org. Chem. 2004, 3201;
30. f) T. Konno, T. Daitoh, A. Noiri, J. Chae, T. Ishihara, H. Yamanaka, Org. Lett. 2004, 6, 933;
31. g) T. Konno, T. Daitoh, A. Noiri, J. Chae, T. Ishihara, H. Yamanaka, Tetrahedron 2005, 61, 9391;
32. h) G. S. Kauffman, P. S. Watson, W. A. Nugent, J. Org. Chem. 2006, 71, 8975;
33. i) P. Sellès, Org. Lett. 2005, 7, 605.
34. Recent examples of transition metal-catalyzed carbozincation of alkynes: a) R. Shintani, T. Yamagami, T. Hayashi, Org. Lett. 2006, 8, 4799;
35. b) R. Shintani, T. Hayashi, Org. Lett. 2005, 7, 2071;
36. c) S. Xue, L. He, Y.-K. Liu, K.-Z. Han, Q.-X. Guo, Synthesis 2006, 666;
37. d) G. Sklute, C. Bolm, I. Marek, Org. Lett. 2007, 9, 1259;
38. e) T. Stüdemann, M. Ibrahim-Ouali, P. Knochel, Tetrahedron 1998, 54, 1299;
39. f) H. Yasui, T. Nishikawa, H. Yorimitsu, K. Oshima, Bull. Chem. Soc. Jpn. 2006, 79, 1271;
40. g) K. Murakami, H. Yorimitsu, K. Oshima, Org. Lett. 2009, 11, 2373.
41. Carbometalation of unfunctionalized alkynes is difficult and there are few examples of carbometalation of dialkylacetylenes. Carbomagnesiation: a) E. Shirakawa, T. Yamagami, T. Kimura, S. Yamaguchi, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 17164;
42. b) K. Murakami, H. Ohmiya, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 1569; carboboration:
43. c) M. Suginome, M. Shirakura, A. Yamamoto, J. Am. Chem. Soc. 2006, 128, 14438;
44. d) M. Daini, M. Suginome, Chem. Commun. 2008, 5224; carbostannylation:
45. e) E. Shirakawa, K. Yamasaki, H. Yoshida, T. Hiyama, J. Am. Chem. Soc. 1999, 121, 10221; carbozincation: reference [6g].
46. Optimization of the reaction was noted in the Supporting Information.
47. Three equivalents of benzylzinc reagents were necessary. Using fewer amounts of benzylzinc reagents resulted in lower yields and slower conversions.
48. Usually, cobalt-catalyzed cyclotrimerization of alkyne requires high temperature, see: a) J. A. Varela, C. Saá, J. Organomet. Chem. 2009, 694, 143;
49. b) L. V. R. Boñaga, H.-C. Zhang, A. F. Moretto, H. Ye, D. A. Gauthier, J. Li, G. C. Leo, B. E. Maryanoff, J. Am. Chem. Soc. 2005, 127, 3473.
50. For examples of acceleration of reaction by adding Li salt, see: a) A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396;
51. Angew. Chem. Int. Ed. 2004, 43, 3333;
52. b) A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 118, 6186;
53. Angew. Chem. Int. Ed. 2006, 45, 6040;
54. c) F. M. Piller, P. Appukkuttan, A. Gavryushin, M. Helm, P. Knochel, Angew. Chem. 2008, 120, 6907;
55. Angew. Chem. Int. Ed. 2008, 47, 6802;
56. c) N. Fujii, K. Nakai, H. Habashita, H. Yoshizawa, T. Ibuka, F. Gerrido, A. Mann, Y. Chounan, Y. Yamamoto, Tetrahedron Lett. 1993, 34, 4227;
57. e) H. Ochiai, M. Jang, K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 2681;
58. f) G. T. Achonduh, N. Hadei, C. Valente, S. Avola. C. J. O'Brien, M. G. Organ, Chem. Commun. 2010, DOI: 10.1039/c002759f.
59. The reason for the dramatic effect of the addition of the lithium and magnesium salts is not clear at this stage.