MgCl2-accelerated addition of functionalized organozinc reagents to aldehydes, ketones, and carbon dioxide

Angewandte Chemie - International Edition

Volumn 49, Issue 27, 2010, Pages 4665-4668

  Metzger, Albrecht ^a   Bernhardt, Sebastian ^a   Manolikakes, Georg ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Carbon dioxide; Carbonyl addition; Ibuprofen; Magnesium chloride; Organozinc reagents

Indexed keywords

CARBONYL ADDITION; DIRECT REACTIONS; FUNCTIONALIZED; MAGNESIUM CHLORIDE; MAGNESIUM CHLORIDES; ORGANOZINC REAGENTS; PHENYLACETIC ACID; ZINC REAGENTS;

ALDEHYDES; CARBON DIOXIDE; CARBONYLATION; CHLORINE COMPOUNDS; KETONES; MAGNESIUM; SYNTHESIS (CHEMICAL); ZINC;

ORGANOMETALLICS;

EID: 77953935511     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000634     Document Type: Article

References (68)

1. a) P. Knochel in Handbook of Functionalized Organometallics, Wiley-VCH, New York, 2005;
2. b) P. Knochel, N. Millot, A. L. Rodriguez, C. E. Tucker, Org. React. 2001, 58, 417;
3. c) A. Boudier, L. O. Bromm, M. Lotz, P. Knochel, Angew. Chem. 2000, 112, 4584;
4. Angew. Chem. Int. Ed. 2000, 39, 4414;
5. d) P. Knochel, J. J. Almena Perea, P. Jones, Tetrahedron 1998, 54, 8275.
6. a) E. Negishi, Acc. Chem. Res. 1982, 15, 340;
7. b) E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc. 1980, 102, 3298;
8. c) X. Zeng, M. Qian, Q. Hu, E. Negishi, Angew. Chem. 2004, 116, 2309;
9. Angew. Chem. Int. Ed. 2004, 43, 2259.
10. a) T. Stüdemann, P. Knochel, Angew. Chem. 1997, 109, 132;
11. Angew. Chem. Int. Ed. Engl. 1997, 36, 93;
12. b) A. Gavryushin, C. Kofink, G. Manolikakes, P. Knochel, Org. Lett. 2005, 7, 4871;
13. c) C. S. Yeung, V. M. Dong, J. Am Chem. Soc 2008, 130, 7826.
14. a) P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390;
15. b) M. C. P. Yeh, P. Knochel, Tetrahedron Lett. 1989, 30, 4799;
16. c) M. C. P. Yeh, P. Knochel, L. E. Santa, Tetrahedron Lett. 1988, 29, 3887.
17. C. K. Reddy, P. Knochel, Angew. Chem. 1996, 108, 1812;
18. Angew. Chem. Int Ed. Engl. 1996, 35, 1700.
19. a) C. Gosmini, Y. Rollin, J. Y. Nédélec, J. Périchon, J. Org. Chem. 2000, 65, 6024;
20. b) H. Fillon, C. Gosmini, J. Périchon, J. Am. Chem. Soc. 2003, 125, 3867;
21. c) I. Kazmierski, M. Bastienne, C. Gosmini, J.-M. Paris, J. Périchon, J. Org. Chem. 2004, 69, 936.
22. a) Y. Tamaru, T. Nakamura, M. Sakaguchi, H. Ochiai, Z. Yoshida, J. Chem. Soc. Chem. Commun. 1988, 610;
23. b) D. Seebach, A. K. Beck, B. Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363.
24. a) J. G. Kim, P. J. Walsh, Angew. Chem. 2006, 118, 4281;
25. Angew. Chem. Int. Ed. 2006, 45, 4175;
26. b) H. Li, P. J. Walsh, J. Am. Chem. Soc. 2005, 127, 8355;
27. c) S.-J. Jeon, H. Li, P. J. Walsh, J. Am. Chem. Soc. 2005, 127, 16416.
28. a) H. Yamamoto, Lewis-Acids in Organic Synthesis, Vol. 2, Wiley-VCH, Weinheim, 2000;
29. b) K. Yearick, C. Wolf, Org. Lett. 2008, 10, 3915;
30. c) M. Hatano, S. Suzuki, K. Ishihara, J. Am. Chem. Soc. 2006, 128, 9998;
31. d) M. Hatano, O. Ito, S. Suzuki, K. Ishihara, Chem. Commun. 2010, 2674;
32. e) M. Hatano, S. Suzuki, K. Ishihara, Synlett 2010, 321;
33. f) M. Hatano, T. Miyamoto, K. Ishihara, Curr. Org. Chem. 2007, 11, 127;
34. g) M. Hatano, K. Ishihara, Synthesis 2008, 1647;
35. h) M. Hatano, K. Ishihara in Acid Catalysis in Modem Organic Synthesis, Vol. 1 (Eds.: H. Yamamoto, K. Ishihara), Wiley-VCH, Weinheim, 2008, pp. 135;
36. i) L. Jin, C. Liu, J. Liu, F. Hu, Y. Lan, A. S. Batsanov, J. A. K. Howard, T. B. Marder, A. Lei, J. Am. Chem. Soc. 2009, 131, 16656.
37. a) For increased reactivity of organometallic reagents through the addition of Mg salts, see: L. A. Paquette in Encyclopedia of Reagents for Organic Synthesis, Vol. 5, Wiley-VCH, New York, 1995, p. 3197;
38. b) B. Marx, E. Henry-Basch, P. Fréon, C. R. Hebd. Seances Acad. Sci. Ser. C 1967, 264, 527.
39. A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 118, 6186;
40. Angew. Chem. Int. Ed. 2006, 45, 6040.
41. F. M. Piller, A. Metzger, M. A. Schade, B. A. Haag, A. Gavryushin, P. Knochel, Chem. Eur. J. 2009, 15, 7192.
42. 2·LiCl (1 h reaction, time) 3 a was obtained in 86% yield.
43. S. Matsubara, T. Ikeda, K. Oshima, K. Utimoto, Chem. Lett. 2001, 1226.
44. 2 (0.55 equiv) in THF at 25°C within 2 h.
45. a) A. Metzger, M. A. Schade, P. Knochel, Org. Lett. 2008, 10, 1107;
46. b) A. Metzger, M. A. Schade, G. Manolikakes, P. Knochel, Chem. Asian J. 2008, 3, 1678.
47. A. Metzger, F. M. Piller, P. Knochel, Chem. Commun. 2008, 5824.
48. 2·LiCl (1.2 equiv) instead of the diarylzinc reagent 6 a (0.6 equiv) led to only 30% conversion of the ketone 2 h under similar reaction conditions.
49. C. Despotopoulou, L. Klier, P. Knochel, Org. Lett. 2009, 11, 3326.
50. a) J. Esquivias, R. G. Arrayás, J. C. Carretero, Angew. Chem. 2007, 119, 9417;
51. Angew. Chem. Int. Ed. 2007, 46, 9257;
52. b) A. Côté, A. B. Charette, J. Am. Chem. Soc. 2008, 130, 2771;
53. c) Using benzylzinc reagent 8 a (1.2 equiv) under similar reaction conditions led to 90% conversion of the aldimine 2 q.
54. K. Kobayashi, Y. Kondo, Org. Lett. 2009, 11, 2035.
55. 2·LiCl instead of the diarylzinc reagent 6 a led to full conversion within 6 h reaction time under similar reaction conditions.
56. A. Garcia Martínez, A. Herrera. Fernández, D. Molero Vilchez, M. L. Laordon Gutiérrez, L. R. Subramanian, Synlett 1993, 229.
57. a) A. R. Bogdan, S. L. Poe, D. C. Kubis, S. J. Broadwater, D. T. McQuade, Angew. Chem. 2009, 121, 8699;
58. Angew. Chem. Int Ed. 2009, 48, 8547;
59. b) Y. Chikusa, T. Fujimoto, M. Ikunaka, T. Inoue, S. Kamiyama, K. Maruo, J. Matsumoto, K. Matsuyama, M. Moriwaki, H. Nohira, S. Saijo, M. Yamanishi, K. Yoshida, Org. Process Res Dev. 2002, 6, 291;
60. c) C. R. Smith, T. V. RajanBabu, J. Org. Chem. 2009, 74, 3066.
61. A patent application has been filed.
62. a) C. Lambert, F. Hampel, P. von R. Schleyer, Angew. Chem. 1992, 104, 1242;
63. Angew. Chem. Int. Ed. Engl. 1992, 31, 1209;
64. b) M. Uchiyama, S. Nakamura, T. Ohwada, M. Nakamura, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 10897.
65. E. Negishi, Chem. Eur. J. 1999, 5, 411.
66. a) Y. N. Belokon, W. Clegg, R. W. Harrington, C. Young, M. North, Tetrahedron 2007, 63, 5287;
67. b) Y. N. Belokon, Pure Appl. Chem. 1992, 64, 1917;
68. c) Y. N. Belokon, W. Clegg, R. W. Harrington, V. I. Maleev, M. North, M. O. Pujol, D. L. Usanov, C. Young, Chem. Eur. J. 2009, 15, 2148.