Co-catalyzed cross-coupling of alkyl halides with tertiary alkyl Grignard reagents using a 1,3-butadiene additive

Journal of the American Chemical Society

Volumn 135, Issue 26, 2013, Pages 9604-9607

  Iwasaki, Takanori ^a   Takagawa, Hiroaki ^a   Singh, Surya P ^b   Kuniyasu, Hitoshi ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-BUTADIENE; CROSS-COUPLINGS; GRIGNARD REAGENT; HIGH SELECTIVITY; IONIC MECHANISMS; LIGAND PRECURSORS; QUATERNARY CARBON; STERICALLY CONGESTED;

CATALYSIS; FUNCTIONAL GROUPS;

BUTADIENE;

1,3 BUTADIENE; ALKYL HALIDE DERIVATIVE; GRIGNARD REAGENT; HALIDE; TERTIARY ALKYL GROUP; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CONTROLLED STUDY; CROSS COUPLING REACTION; ISOMERIZATION; PRECURSOR; STEREOCHEMISTRY;

BUTADIENES; CATALYSIS; COBALT; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84879744985     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja404285b     Document Type: Article

References (53)

1. Cárdenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384
2. Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525
3. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674
4. Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937
5. Hu, X. L. Chem. Sci 2011, 2, 1867
6. Hayashi, T.; Konishi, M.; Yokota, K.-i.; Kumada, M. Chem. Lett. 1980, 767
7. Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599
8. Scott, R. S.; Kochi, J. K. J. Org. Chem. 1976, 41, 502
9. Bell, T. W.; Hu, L.-Y.; Patel, S. V. J. Org. Chem. 1987, 52, 3847
10. Cahiez, G.; Avedissian, H. Tetrahedron Lett. 1998, 39, 6159
11. Cahiez, G.; Avedissian, H. Synthesis 1998, 1199
12. Hintermann, L.; Xiao, L.; Labonne, A. Angew. Chem., Int. Ed. 2008, 47, 8246
13. Lohre, C.; Dröge, T.; Wang, C.; Glorius, F. Chem.-Eur. J. 2011, 17, 6052
14. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478
15. Burns, D. H.; Miller, J. D.; Chan, H.-K.; Delaney, M. O. J. Am. Chem. Soc. 1997, 119, 2125
16. Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61
17. Cahiez, G.; Chaboche, C.; Jézéquel, M. Tetrahedron 2000, 56, 2733
18. Terao, J.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2003, 125, 5646
19. Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086
20. Cahiez, G.; Gager, O.; Buendia, J. Synlett 2010, 299
21. Yang, C.-T.; Zhang, Z.-Q.; Liang, J.; Liu, J.-H.; Lu, X.-Y.; Chen, H.-H.; Liu, L. J. Am. Chem. Soc. 2012, 134, 11124
22. Ren, P.; Stern, L.-A.; Hu, X. L. Angew. Chem., Int. Ed. 2012, 51, 9110
23. Tamao, K.; Kiso, Y.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9268
24. Terao, J.; Kambe, N. Bull. Chem. Soc. Jpn. 2006, 79, 663
25. Terao, J.; Kambe, N. Acc. Chem. Res. 2008, 41, 1545
26. Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222
27. Terao, J.; Naitoh, Y.; Kuniyasu, H.; Kambe, N. Chem. Lett. 2003, 32, 890
28. Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem., Int. Ed. 2004, 43, 6180
29. Singh, S. P.; Terao, J.; Kambe, N. Tetrahedron Lett. 2009, 50, 5644
30. Singh, S. P.; Iwasaki, T.; Terao, J.; Kambe, N. Tetrahedron Lett. 2011, 52, 774
31. Iwasaki, T.; Tsumura, A.; Omori, T.; Kuniyasu, H.; Terao, J.; Kambe, N. Chem. Lett. 2011, 40, 1024
32. Shen, R.; Iwasaki, T.; Terao, J.; Kambe, N. Chem. Commun. 2012, 48, 9313
33. Iwasaki, T.; Higashikawa, K.; Reddy, V. P.; Ho, W. W. S.; Fujimoto, Y.; Fukase, K.; Terao, J.; Kuniyasu, H.; Kambe, N. Chem.-Eur. J. 2013, 19, 2956
34. Ghaderi, A.; Iwasaki, T.; Fukuoka, A.; Terao, J.; Kambe, N. Chem.-Eur. J. 2013, 19, 2951
35. Yorimitsu, H.; Oshima, K. Pure Appl. Chem. 2006, 78, 441
36. Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435
37. Cahiez, G.; Chaboche, C.; Duplais, C.; Giulliani, A.; Moyeux, A. Adv. Synth. Catal. 2008, 350, 1484
38. Zhou, W.; Napoline, J. W.; Thomas, C. M. Eur. J. Inorg. Chem. 2011, 2029
39. Tsuji, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2002, 41, 4137
40. Ohmiya, H.; Tsuji, T.; Yorimitsu, H.; Oshima, K. Chem.-Eur. J. 2004, 10, 5640
41. Someya, H.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 1565
42. Someya, H.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Tetrahedron 2007, 63, 8609
43. Todo, H.; Terao, J.; Watanabe, H.; Kuniyasu, H.; Kambe, N. Chem. Commun. 2008, 1332
44. Tamura, M.; Kochi, J. Synthesis 1971, 303
45. Cahiez, G.; Alami, M. Tetrahedron 1989, 45, 4163
46. 2·2LiI: see ref 8a
47. Torrens, H. Coord. Chem. Rev. 2005, 249, 1957
48. Terao, J.; Todo, H.; Watabe, H.; Ikumi, A.; Shinohara, Y.; Kambe, N. Pure Appl. Chem. 2008, 80, 941
49. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119
50. -1, respectively, see: Maillard, B.; Forrest, D.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 7024
51. Allegra, G.; Giudice, F. L.; Natta, G.; Giannini, U.; Fagherazzi, G.; Pino, P. Chem. Commun. 1967, 1263
52. Bönnemann, H.; Bogdanović, B.; Brinkmann, R.; Spliethoff, B.; He, D.-W. J. Organomet. Chem. 1993, 451, 23
53. Crewdson, P.; Bryce, D. L.; Rominger, F.; Hofmann, P. Angew. Chem., Int. Ed. 2008, 47, 3454