Simplifying nickel(0) catalysis: An air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes

Journal of the American Chemical Society

Volumn 135, Issue 4, 2013, Pages 1585-1592

  Standley, Eric A ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; ALLYLBENZENE; BENZYLATION; HIGH YIELD; NICKEL COMPLEX; PRECATALYSTS; ROOM TEMPERATURE; SELECTIVE COUPLING; SUBSTITUTED BENZYL CHLORIDES; TERMINAL ALKENES;

CHLORINE COMPOUNDS; NICKEL; NICKEL COMPOUNDS; OLEFINS; PURIFICATION; SYNTHESIS (CHEMICAL);

AIR CLEANERS;

ALKENE; BENZYL CHLORIDE; NICKEL; WATER;

AIR; ARTICLE; BENZYLATION; CATALYSIS; CHEMICAL REACTION; ROOM TEMPERATURE; SYNTHESIS;

AIR; ALKENES; ALLYL COMPOUNDS; BENZENE DERIVATIVES; CATALYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS;

EID: 84873883449     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3116718     Document Type: Article

References (71)

1. Knowles, J. P; Whiting, A. Org. Biomol. Chem. 2007, 5, 31-44
2. Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 5.
3. Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 6.
4. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066
5. Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945-2964
6. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518-5526
7. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581-581
8. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320-2322
9. For an overview of the state of regiocontrol of the Heck reaction through 2009, see Nilsson, P.; Olofsson, K.; Larhed, M. In The Mizoroki-Heck Reaction; Oestreich, M., Ed.; Wiley: Chichester, U.K., 2009; Chapter 3, pp 133-162.
10. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419
11. Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751-760
12. Ruan, J.; Xiao, J. Acc. Chem. Res. 2011, 44, 614-626
13. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558-3563
14. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1993, 58, 7421-7126
15. Olofsson, K.; Larhed, M.; Hallberg, A. J. Org. Chem. 2000, 65, 7235-7239
16. Olofsson, K.; Sahlin, H.; Larhed, M.; Hallberg, A. J. Org. Chem. 2001, 66, 544-549
17. Matsubara, R.; Gutierrez, A. C.; Jamison, T. F. J. Am. Chem. Soc. 2011, 133, 19020-19023
18. Qin, L.; Ren, X.; Lu, Y.; Li, Y.; Zhou, J. Angew. Chem., Int. Ed. 2012, 51, 5915-5919
19. Werner, E. W.; Sigman, M. S. J. Am. Chem. Soc. 2011, 133, 9692-9695
20. Zheng, C.; Wang, D.; Stahl, S. S. J. Am. Chem. Soc. 2012, 134, 16496-16499
21. Wong, P. K.; Lau, K. S. Y.; Stille, J. K. J. Am. Chem. Soc. 1974, 96, 5956-5957
22. Wu, G.-z.; Lamaty, F.; Negishi, E.-i. J. Org. Chem. 1989, 54, 2507-2508
23. Yi, P.; Zhuangyu, Z.; Hongwen, H. Synth. Commun. 1992, 22, 2019-2029
24. Yi, P.; Zhuangyu, Z.; Hongwen, H. Synthesis 1995, 245-247
25. Kumar, P. Org. Prep. Proced. Int. 1997, 29, 477-480
26. Wang, L.; Pan, Y.; Jiang, X.; Hu, H. Tetrahedron Lett. 2000, 41, 725-727
27. Narahashi, H.; Yamamoto, A.; Shimizu, I. Chem. Lett. 2004, 33, 348-349
28. Narahashi, H.; Shimizu, I.; Yamamoto, A. J. Organomet. Chem. 2008, 693, 283-296
29. Yang, Z.; Zhou, J. J. Am. Chem. Soc. 2012, 134, 11833-11835
30. 2, see Wilke, G. Angew. Chem. 1960, 72, 581-582
31. The crystal structure was determined and reported in Dierks, H.; Dietrich, H. Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem. 1965, 122, 1-23
32. 3Al as the reductant, see Bogdanović, B.; Kröner, M.; Wilke, G. Justus Liebigs Ann. Chem. 1966, 699, 1-23
33. A modification was devised and reported in Semmelhack, M. F. Org. React. 1972, 19, 115-198
34. A detailed, further modified procedure was later reported: Schunn, R. A. Inorg. Synth. 1974, 15, 5-9
35. A more convenient preparation using DIBAL as the reductant was reported in Krysan, D. J.; Mackenzie, P. B. J. Org. Chem. 1990, 55, 4229-4230
36. Herrmann, G.; Wilke, G. Angew. Chem. 1962, 17, 693-694
37. 2)Ni(0) exists in solution coordinated to solvent or allylbenzene, rather than as a discrete species. There is evidence that two-coordinate nickel(0) species do exist in solution but only with very large NHC ligands such as IPr. For an example, see Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. J. Am. Chem. Soc. 2002, 124, 15188-15189
38. Chatt, J.; Shaw, B. L. J. Chem. Soc. 1960, 1718-1729
39. Cross, R. J.; Wardle, R. J. Chem. Soc. A 1970, 840-845
40. Cassar, L.; Ferrara, S.; Foá, M. In Advances in Chemistry Series; American Chemical Society: Washington, DC; 1974; Vol. 132, pp 252-273.
41. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: New York, 1998; pp 3-4.
42. Chen, C.; Yang, L.-M. Tetrahedron Lett. 2007, 48, 2427-2430
43. Gao, C.-Y.; Yang, L.-M. J. Org. Chem. 2008, 73, 1624-1627
44. Lanni, E. L.; Locke, J. R.; Gleave, C. M.; McNiel, A. J. Macromolecules 2011, 44, 5136-5145
45. Zhang, N.; Hoffman, D. J.; Gutsche, N.; Gupta, J.; Percec, V. J. Org. Chem. 2012, 77, 5956-5964
46. Leowanawat, P.; Zhang, N.; Safi, M.; Hoffman, D. J.; Fryberger, M. C.; George, A.; Percec, V. J. Org. Chem. 2012, 77, 2885-2892
47. Masahiro, U.; Yves, C.; Gilles, L. C. R. Seances Acad. Sci., Ser. C 1967, 265, 103-106
48. A more rigorous characterization of the complex and a number of related complexes was carried out: Stone, P. J.; Zvi, D. Inorg. Chim. Acta 1970, 5, 434-438
49. An excellent overview of these techniques is provided in Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346-1416
50. Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, M.; Fujioka, A.; Kodama, S.-i.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969
51. Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422-14423
52. For an example using MeMgBr, see Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054-6058. Other mechanisms of reduction are possible: the use of n -BuLi as the reductant yields a mixture of n -butane, 1-butene, and n -octane. A discussion of this topic is found in ref 19.
53. Herath, A.; Li, W.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 469-471
54. Li, W.; Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2009, 131, 17024-17029
55. Phillips, J. H.; Montgomery, J. Org. Lett. 2010, 12, 4556-4559
56. Beaver, M. G.; Jamison, T. F. Org. Lett. 2012, 13, 4140-4143
57. Bower, J. F.; Skucas, E.; Patman, R. L.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 15134-15135
58. Bower, J. F.; Patman, R. L.; Krische, M. J. Org. Lett. 2008, 10, 1033-1035
59. Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338-6339
60. Patman, R. L.; Chaulagain, M. R.; Williams, V. M.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2066-2067
61. Miller, J. S.; Pokhodnya, K. I. J. Mater. Chem. 2007, 17, 3585-3587
62. Takahashi, S.; Suzuki, Y.; Hagihara, N. Chem. Lett. 1974, 1363-1366
63. Eisch, J. J.; Qian, Y.; Singh, M. J. Organomet. Chem. 1996, 512, 207-217
64. Csok, Z.; Vechorkin, O.; Harkins, S. B.; Scopelliti, R.; Hu, X. L. J. Am. Chem. Soc. 2008, 130, 8156-8157
65. Vechorkin, O.; Hu, X. L. Angew. Chem., Int. Ed. 2009, 48, 2937-2940
66. Vechorkin, O.; Csok, Z.; Scopelliti, R.; Hu, X. L. Chem.-Eur. J. 2009, 15, 3889-3899
67. Nickel hydrides (such as complex 47, Scheme 7) are known to isomerize alkenes, which can under some circumstances cause a small amount of isomerization of the starting alkene to form the corresponding cis-or trans -2-alkene. In these instances, between 0% and 5% of the recovered starting alkene is isolated as this isomer. For a recent example of a nickel hydride used for alkene isomerization, see Lim, H. J.; Smith, C. R.; RajanBabu, T. V. J. Org. Chem. 2009, 74, 4565
68. For an example of a Ni(0)-catalyzed cross-coupling reaction of an unactivated aryl fluoride, see Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 19505-19511
69. A room-temperature, nickel(0)-catalyzed Suzuki-Miyaura reaction of unactivated aryl chlorides has been described: Tang, Z. Y.; Hu, Q. S. J. Org. Chem. 2006, 71, 2167-2169
70. Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 6319-6332
71. Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 2.