Cross-coupling of aryl/alkenyl pivalates with organozinc reagents through nickel-catalyzed C-O bond activation under mild reaction conditions

Angewandte Chemie - International Edition

Volumn 47, Issue 52, 2008, Pages 10124-10127

  Li, Bi Jie ^b   Li, Yi Zhou ^b   Lu, Xing Yu ^b   Liu, Jia ^b   Guan, Bing Tao ^b   Shi, Zhang Jie ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

C O activation; Cross coupling; Homogeneous catalysis; Nickel; Organozinc reagents

Indexed keywords

CATALYSIS; NICKEL; NICKEL ALLOYS; REACTION KINETICS;

BOND ACTIVATIONS; C-O ACTIVATION; CATALYST SYSTEMS; CROSS-COUPLING; CYCLOHEXYL; HIGH EFFICIENCIES; HOMOGENEOUS CATALYSIS; MILD REACTION CONDITIONS; ORGANOZINC REAGENTS;

ORGANOMETALLICS;

CARBON; NICKEL; ORGANOMETALLIC COMPOUND; OXYGEN; PIVALIC ACID; VALERIC ACID DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY;

CARBON; CATALYSIS; NICKEL; ORGANOMETALLIC COMPOUNDS; OXYGEN; PENTANOIC ACIDS; ZINC;

EID: 57749092886     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803814     Document Type: Article

References (73)

1. a) Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998;
2. b) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
3. c) Cross-coupling Reactions: A Practical Guide (Ed.: N. Miyaura), Springer, Berlin, 2002.
4. a) M. Kertesz, C. H. Choi, S. Yang, Chem. Rev. 2005, 105, 3448;
5. b) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633.
6. a) A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350;
7. Angew. Chem. Int. Ed. 2002, 41, 4176;
8. b) C. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719;
9. c) J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc. 2004, 126, 13028;
10. d) Z.-Y. Tang, Q.-S. Hu, J. Am. Chem. Soc. 2004, 126, 3058;
11. e) L.Wang, Z.-X.Wang, Org. Lett. 2007, 9, 4335;
12. f) Z. Xi, B. Liu, W. Chen, J. Org. Chem. 2008, 73, 3954;
13. g) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem. 1995, 107, 1992;
14. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848;
15. h)W. Shen, Tetrahedron Lett. 1997, 38, 5575;
16. i) A. F. Littke, L. Schwarz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343;
17. j) J. Huang, S. P. Nolan, J. Am. Chem. Soc. 1999, 121, 9889;
18. k) G. Altenhoff, R. Goddard, C.W. Lehmann, F. Glorius, J. Am. Chem. Soc. 2004, 126, 15195;
19. l) L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681;
20. Angew. Chem. Int. Ed. 2006, 45, 2619;
21. m) L. Ackermann, Synlett 2007, 507;
22. n) C. M. So, Z. Zhou, C. P. Lau, F. Y. Kwong, Angew. Chem. 2008, 120, 6502;
23. Angew. Chem. Int. Ed. 2008, 47, 6402;
24. o) R. H. Munday, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2008, 130, 2754;
25. p) L. Zhang, J. Wu, J. Am. Chem. Soc. 2008, 130, 12250;
26. q) L. Zhang, J. Qing, P. Yang, J. Wu, Org. Lett. 2008, 10, 4971.
27. a) A. Fürstner, A. Leitner, M. Mendez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13 856;
28. b) M. Tamura, J. Kochi, J. Am. Chem. Soc. 1971, 93, 1487;
29. c) M. Tamura, J. Kochi, Synthesis 1971, 303;
30. d) M. S. Kharasch, E. K. Fields, J. Am. Chem. Soc. 1941, 63, 2316;
31. e) C. Gosmini, J.-M. Bégouin, A. Moncomble, Chem. Commun. 2008, 3221;
32. f) T. J. Korn, P. Knochel, Angew. Chem. 2005, 117, 3007;
33. Angew. Chem. Int. Ed. 2005, 44, 2947;
34. g) V. Percec, J.-Y. Bae, M. Zhao, D. H. Hill, J. Org. Chem. 1995, 60, 176.
35. a) A. Zapf, Angew. Chem. 2003, 115, 5552;
36. Angew. Chem. Int. Ed. 2003, 42, 5394;
37. b) Y. Matsuura, M. Tamura, T. Kochi, M. Sato, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007, 129, 9858;
38. c) for the coupling of benzylic acetate, see: R. Kuwano, M. Yokogi, Chem. Commun. 2005, 5899, and references therein.
39. a)W. A. Reckhow, D. S. Tarbell, J. Am. Chem. Soc. 1952, 74, 4968;
40. b) K. Miura, H. Saito, N. Fujisawa, D. Wang, H. Nishikori, A. Hosomi, Org. Lett. 2001, 3, 4055.
41. a) E. Wenkert, E. L. Michelotti, C. S. Swindell, J. Am. Chem. Soc. 1979, 101, 2246;
42. b) E. Wenkert, E. L. Michelotti, C. S. Swindell, M. Tingoli, J. Org. Chem. 1984, 49, 4894;
43. c) J. W. Dankwardt, Angew. Chem. 2004, 116, 2482;
44. Angew. Chem. Int. Ed. 2004, 43, 2428;
45. d) F. Kakiuchi, M. Usui, S. Ueno, N. Chatani, S. Murai, J. Am. Chem. Soc. 2004, 126, 2706;
46. e) M. Tobisu, T. Shimasaki, N. Chatani, Angew. Chem. 2008, 120, 4944;
47. Angew. Chem. Int. Ed. 2008, 47, 4866;
48. f) B. Guan, S. Xiang, T. Wu, B. Wang, K. Zhao, Z. Shi, Chem. Commun. 2008, 1437;
49. g) B.-T. Guan, S.-K. Xiang, B.-Q. Wang, Z.-P. Sun, Y. Wang, K.-Q. Zhao, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 3268.
50. B.-T. Guan, Y. Wang, B.-J. Li, D.-G. Yu, Z.-J. Shi, J. Am. Chem. Soc. 2008, 130, 14468.
51. a) Organozinc Reagents, A Practical Approach (Eds.: P. Knochel, P. Jones), Oxford, New York, 1999;
52. b) E. Erdik, Organozinc Reagents in Organic Synthesis; CRC, Boston, 1996.
53. a) M. Palucki, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 3395;
54. b) J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852;
55. c) P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808;
56. Angew. Chem. Int. Ed. 2004, 43, 4704;
57. d) M. Seno, S. Tsuchiya, M. Hidai, Y. Uchida, Bull. Chem. Soc. Jpn. 1976, 49, 1184.
58. a) L. Boymond, M. Rottländer, G. Cahiez, P. Knochel, Angew. Chem. 1998, 110, 1801;
59. Angew. Chem. Int. Ed. 1998, 37, 1701;
60. b) A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396;
61. Angew. Chem. Int. Ed. 2004, 43, 3333.
62. a) Y. Kiso, K. Tamao, M. Kumada, J. Organomet. Chem. 1973, 50, C12;
63. b) V. P. W. Böhm, C.W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, Angew. Chem. 2001, 113, 3500;
64. Angew. Chem. Int. Ed. 2001, 40, 3387;
65. c) Y. M. Kim, S. Yu, J. Am. Chem. Soc. 2003, 125, 1696;
66. d) L. Ackermann, R. Born, J. H. Spatz, D. Meyer, Angew. Chem. 2005, 117, 7382;
67. Angew. Chem. Int. Ed. 2005, 44, 7216;
68. e) N. Yoshikai, H. Mashima, E. Nakamura, J. Am. Chem. Soc. 2005, 127, 17978;
69. f) T. J. Korn, M. A. Schade, S. Wirth, P. Knochel, Org. Lett. 2006, 8, 725;
70. g) T. Schaub, P. Fischer, A. Steffen, T. Braun, U. Radius, A. Mix, J. Am. Chem. Soc. 2008, 130, 9304.
71. a) D. Zim, V. R. Lando, J. Dupont, A. L. Monteiro, Org. Lett. 2001, 3, 3049;
72. b) V. Percec, J.-Y. Bae, D. H. Hill, J. Org. Chem. 1995, 60, 6895;
73. c) Y. Murakami, T. Yamamoto, Inorg. Chem. 1997, 36, 5682.