Transition metal catalyzed alkylation at sp3-, sp2-, and sp-carbons

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 69, Issue 11, 2011, Pages 1271-1281

  Kambe, Nobuaki ^a   Terao, Jun ^b   Iwasaki, Takanori ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; CATALYSTS; METAL COMPLEXES; METAL HALIDES; METALS; TRANSITION METAL COMPOUNDS;

ALKYLATION REACTIONS; CARBOMETALATION; CATALYTIC SPECIES; CROSS-COUPLINGS; ELECTRON TRANSFER PROCESS; GRIGNARD REAGENT; TRANSITION METAL CATALYSTS; UNSATURATED BONDS;

TRANSITION METALS;

EID: 84855767272     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.69.1271     Document Type: Article

References (72)

1. For recent reviews of synthetic applications of cross-coupling reactions, see for example; (a) Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177
2. (b) Torborg, G.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027.
3. Ariafard, A.; Lin, Z. Organometallics 2006, 25, 4030.
4. Abis, L.; Sen, A.; Halpern, J. J. Am. Chem. Soc. 1978,100, 2915.
5. Kharasch, M. S.; Fuchs, C. F. J. Am. Chem. Soc. 1943,65, 504.
6. (a) Tamura, M.; Kochi, J. J. Am. Chem. Soc. 1971, 93, 1487
7. (b) Corriu, R. J. P.; Masse, J. P. J. Chem. Soc, Chem. Commun. 1972, 144.
8. (c) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc 1972, 94, 4374
9. (d) Yamamura, M.; Moritani, I.; Murahashi, S.-I. J. Organomet. Chem. 1975, 91, C39.
10. Kambe, R.; Iwasaki, T.; Terao, J. Chem. Soc Rev. 2011, 40, 4937 and references cited therein.
11. Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, R J. Am. Chem. Soc. 2002,124,4222.
12. For seminal papers on cross-coupling reaction using alkyl chlorides, see: (a) Kirchhoff, J. H.; Dai, G.; Fu, G. C Angew. Chem. Int. Ed. 2002, 41, 1945
13. (b) Frisch, A. G.; Shaikh, R.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2002, 41,4056
14. (c) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004,126, 3686.
15. (a) Terao, J.; Ikumi, A.; Kuniyasu, H.; Kambe, R J. Am. Chem. Soc. 2003, 125, 5646
16. (b) Terao, J.; Todo, H.; Watabe, H.; Ikumi, A.; Shinohara, Y.; Kambe, R Pure Appl. Chem. 2008,80, 941.
17. Amii, H.; Uneyama, K. Chem. Rev. 2009,109,2119.
18. Terao, J.; Naitoh, Y.; Kuniyasu, H.; Kambe, R Chem. Lett. 2003, 32, 890.
19. Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem. Int. Ed. 2004, 43, 6180.
20. For transition metal catalyzed Negishi coupling using alkyl halides, see for example: (a) Devasagayaraj, A.; Stüdemann, T; Knöchel, P. Angew. Chem., Int. Ed Engl. 1995, 34, Tili
21. (b) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003,125, 12527
22. (c) Nakamura, M.; Ito, S.; Matsuo, K.; Nakamura, E. Synlett 2005, 1794
23. (d) Takahashi, H.; Inagaki, S.; Nishihara, Y.; Shibata, T.; Takagi, K. Org. Lett. 2006, 8, 3037
24. (e) Gong, H.; Sinisi, R.; Gagne, M. R. J. Am. Chem. Soc. 2007, 129, 1908.
25. Benn, R.; Büssemeier, B.; Holle, S.; Jolly, P. W; Mynott, R.; Tkatchenko, I.; Wilke, G. J. Organomet. Chem. 1985,279, 63.
26. (a) Kaschube, W; Pörschke, K. R.; Angermund, K.; Krüer, C.; Wilke, G. Chem. Ber. 1988,121, 1921
27. (b) Holle, S.; Jolly, P. W; Mynott, R.; SaIz, R. Z. Naturforsch., B: Anorg Chem. Org Chem. 1982,37, 675.
28. 2CuLi) react with R'X to give R-R' via Cu(III) intermediates (a) Bertz, S. H.; Cope, S.; Dorton, D.; Murphy, M.; Ogle, C. A. Angew. Chem. Int. Ed. 2007, 46, 7082
29. (b) Gartner, T.; Yoshikai, R.; Neumeier, M.; Nakamura, E.; Gschwind, R. M. Chem. Commun. 2010, 46, 4625. According to ref. 7, a radical mechanism via an electron transfer from the ate complex 4 to alkyl halides would not be likely.
30. Terao, J.; Naitoh, Y.; Kuniyasu, H.; Kambe, R Chem. Commun. 2007, 825.
31. Pratt, L. M.; Voit, S.; Okeke, F. R.; Kambe, R J. Phys. Chem. A 2011, 115, 2281.
32. Singh, S. P.; Terao, J.; Kambe, N. Tetrahedron Lett. 2009, 50, 5644.
33. Singh, S. P.; Iwasaki, T.; Terao, J.; Kambe, N. Tetrahedron Lett. 2011, 52, 774.
34. Ley and co-workers demonstrated that Pd-containing perovskites exhibit high catalytic activities on heating and can be recovered and reused as catalysts for the Suzuki-Miyaura cross-coupling of aryl halides with aryl- or vinylboronic acids in alcohol solvents in the presence of a base (a) Smith, M. D.; Stepan, A. F.; Ramarao, C.; Brennan, P. E.; Ley, S. V. Chem. Commun. 2003, 2652
35. (b) Andrews, S. P.; Stepan, A. F.; Tanaka, H.; Ley, S. V.; Smith, M. D. Adv. Synth. Catal. 2005,347, 647.
36. Iwasaki, T.; Tsumura, A.; Omori, T.; Kuniyasu, H.; Terao, J.; Kambe, R Chem. Lett., 2011, 40, 1024.
37. Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem. Int. Ed. 2003, 42, 5749.
38. Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, R Angew. Chem. Int. Ed. 2007,46, 2086.
39. The reaction of lithium diorganocuprates with secondary alkyl iodides may generate a radical intermediate (a) Ashby, E. C.; Coleman, D. J. Org. Chem. 1987,52,4554
40. (b) Ashby, E. C.; Depriest, R. R.; Tuncay, A.; Srivastava, S. Tetrahedron Lett. 1982,23, 5251.
41. Maillard, B.; Forrest, D.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7024.
42. Mori, S.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000,122, 7294.
43. (a) Schulte, P.; Behrens, U. J. Organomet. Chem. 1998, J65, 235
44. (b) Miyashita, A.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc Jpn. 1977, 50, 1109.
45. (a) Terao, J.; Kambe, N. Bull. Chem. Soc Jpn. 2006, 79, 663
46. (b) Terao, J.; Kambe, R Chem. Record. 2007, 7, 57
47. (c) Terao, J.; Torii, K.; Saito, K.; Kambe, R.; Baba, A.; Sonoda, R Angew. Chem. Int. Ed. 1998,37, 2653
48. (d) Terao, J.; Jin, Y.; Torii, K.; Kambe, N. Tetrahedron 2004,60, 1301.
49. Negishi, E.; Nguyen, T.; Maye, J. P.; Choueiri, D.; Suzuki, N.; Takahashi, T. Chem Lett. 1992, 2367.
50. (a) Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829
51. (b) Negishi, E.; Swanson, D. R.; Takahashi, T. J. Chem. Soc, Chem Commun. 1990, 1254.
52. Terao, J.; Begum, S. A.; Oda, A.; Kambe, N. Synlett 2005,1783.
53. Terao, J.; Watabe, H.; Watanabe, H.; Kambe, R Adv. Synth. Catal. 2004,546,1674.
54. (a) Terao, J.; Saito, K.; Nii, S.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1998, 120, 11822
55. (b) Nii, S.; Terao, J.; Kambe, N. J. Org Chem. 2000, 65, 5291.
56. Terao, J.; Watabe, H.; Miyamoto, M.; Kambe, R Bull. Chem. Soc Jpn. 2003, 76, 2209.
57. Terao, J.; Kato, Y.; Kambe, N. Chem. Asian J. 2008,5, 1472.
58. Terao, J.; Nii, S.; Chowdhury, E. A.; Nakamura, A.; Kambe, R Adv. Synth. Catal. 2004,346, 905.
59. Kambe, R.; Moriwaki, Y.; Fujii, Y.; Iwasaki, T.; Terao, J. Org. Lett. 2011, 13,4656.
60. 2Ag • MgX) are known to add to enynes: Westmijze, H.; Kleijn, H.; Vermeer, P. J. Organomet. Chem. 1982,254, 117.
61. Terao, J.; Watabe, H.; Kambe, N. J. Am. Chem. Soc. 2005, 127, 3656.
62. Fujii, Y.; Terao, J.; Watabe, H.; Watanabe, H.; Kambe, R Tetrahedron 2007,63, 6635.
63. Fujii, Y.; Terao, J.; Kato, Y; Kambe, R Chem. Commun. 2008, 5836.
64. 2 reacts with vinyl lithium in the presence of TMEDA to yield butadiene (a) Beckhaus, R.; Thiele, K.-H.; J. Organomet. Chem. 1986, 317, 23
65. (b) Beckhaus, R.; Flatau, S.; Trojanov, S.; Hofmann, P. Chem. Ber. 1992, 125, 291
66. (c) Beckhaus, R. Angew. Chem., Int. Ed Engl. 1997,36, 686.
67. 2Ti(η-allyl)X complex has been reported (a) Sato, E.; lida, K.; Iijima, S.; Morita, H.; Sato, M. J. Chem. Soc, Chem. Commun. 1981, 1140
68. (b) Hanzawa, Y.; Kowase, R.; Taguchi, T Tetrahedron Lett. 1998, 39, 583
69. (c) Hanzawa, Y; Kowase, R.; Momose, S.; Taguchi, T. Tetrahedron 1998,54, 11387.
70. Todo, H.; Terao, X.; Watanabe, H.; Kuniyasu, H.; Kambe, N. Chem. Commun. 2008, 1332.
71. Fujii, Y.; Terao, X.; Kambe, R Chem. Commun. 2009, 1115.
72. Fujii, Y; Terao, X.; Kuniyasu, H.; Kambe, N. J. Organomet. Chem. 2007,692, 375.