Nickel-Catalyzed reductive cross-Coupling of unactivated alkyl halides

Organic Letters

Volumn 13, Issue 8, 2011, Pages 2138-2141

  Yu, Xiaolong ^a   Yang, Tao ^a   Wang, Shulin ^a   Xu, Hailiang ^a   Gong, Hegui ^a  

^a SHANGHAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955398877     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200617f     Document Type: Article

References (52)

1. For selected reviews, see: Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656-2670.
2. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
3. For recent examples on Ni-Catalyzed asymmetrical cross-couplings of alkyl halides,
4. see: Lou, S.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 1264-1266.
5. Lou, S.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 5010-5011.
6. Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11908-11909.
7. For recent examples of Pd-, Cu-, and Fe-catalyzed cross-couplings on alkyl electrophiles.
8. see: He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524-2525.
9. Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086-2089.
10. Hatakeyama, T.; Hashimoto, T.; Kondo, Y.; Fujiwara, Y.; Seike, H.; Takaya, H.; Tamada, Y.; Ono, T.; Nakamura, M. J. Am. Chem. Soc. 2010, 132, 10674-10676.
11. Fürstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773-8787.
12. For recent examples of catalytic coupling of Ar-Ar halides.
13. see: Lee, K.; Lee, P. H. Tetrahedron Lett. 2008, 49, 4302-4305.
14. Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 71, 1284-1287.
15. Gosmini, C.; Bassene-Ernst, C.; Durandetti, M. Tetrahedron 2009, 65, 6141-6146.
16. Wang, L.; Lu, W. Org. Lett. 2009, 11, 1079-1082.
17. Amatore, M.; Gosmini, C. Angew. Chem., Int. Ed. 2008, 47, 2089-2092.
18. For the coupling of alkyl with aryl or alkenyl halides.
19. see: Czaplik, W. M.; Mayer, M.; Grupe, S.; von Wangelin, A. J. Pure Appl. Chem. 2010, 82, 1545-1553.
20. Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920-921.
21. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592-15593.
22. Czaplik, W. M.; Mayer, M.; von Wangelin, A. J. Angew. Chem., Int. Ed. 2009, 48, 607-610.
23. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. Org. Lett. 2010, 12, 4742-4744.
24. For catalytic homocoupling of two alkyl electrophiles.
25. see: Prinsell, M. R.; Everson, D. A.; Weix, D. J. Chem. Commun. 2010, 5743-5745. and references cited therein
26. Goldup, S. M.; Leigh, D. A.; McBurney, R. T.;McGonigal, P.R.; Plant, A. Chem Sci 2010, 1, 383-386.
27. The Ni(COD)2/(S)-sBu-Pybox 3a catalytic system has proven to be highly efficient for the Negishi coupling of unactivated alkyl halides with primary alkylzincs: Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726-14727.
28. For other selected examples of Ni/Pybox-catalyzed Negishi couplings.
29. see: Lundin, P. M.; Esquivias, J.; Fu, G. C. Angew. Chem., Int. Ed. 2009, 48, 154-156.
30. Gong, H.; Sinisi, R.; Gagné, M. R. J. Am. Chem. Soc. 2007, 129, 1908-1909.
31. DMA of extra dry (Acros), extra pure (99.5%, Acros), and AR grade (Aladdin Co., China, $8/1 L) qualities gave similar yields. The details of the effects of water and acids are provided in Table S7 (Supporting Information).
32. See the Supporting Information for details.
33. In addition to refs 2a-2c, other non-Pybox ligands have also been used in the Ni-catalyzed cross-coupling of alkyl halides to avoid β-H elimination: Breitenfeld, J.; Vechorkin, O.; Corminboeuf, C.; Scopelliti, R.; Hu, X. Organometallics 2010, 29, 3686-3689.
34. Smith, S. W.; Fu, G. C. Angew. Chem., Int. Ed. 2008, 47, 9334-9336.
35. Gong, H.; Gagné, M. R. J. Am. Chem. Soc. 2008, 130, 12177-12183.
36. Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789.
37. Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79-85.
38. Huo, S. Org. Lett. 2003, 5, 423-425.
39. With the use of 5% and 10% I2 or 8% 3a as activation reagents, the percent conversion of the starting 5-iodopentyl benzoate (0.47Min DMA) to the organozinc reagent was 0.22, 68, and 45 after 3 h, respectively.
40. Knochel has demonstrated that 73% of OctZnBr 3 LiCl is protonated after 5 min with 1 equiv of iPr-OH, and using phenol as the proton source led to an instant complete hydrolysis of octylzinc bromide after 30 s: Manolikakes, G.; Hernandez, C. M.; Matthias, A.; Schade, M. A.; Metzger, A.; Knochel, P. J. Org. Chem. 2008, 73, 8422-8436.
41. Under Ni-catalyzed Negishi conditions, a 1:3:3 mixture of 1, benzoyloxypentyl zinc bromide, and 4-Br-phenol only gave recovered 1.
42. González-Bobes, F.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 5360-5361.
43. Gong, H.; Andrews, R. S.; Zuccarello, J. L.; Lee, S. J.; Gagné, M. R. Org. Lett. 2009, 11, 879-882.
44. III intermediates.
45. see: Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547-7560.
46. Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627-2637.
47. Amatore, C.; Jutand, A. Organometallics 1988, 7, 2203-2214.
48. Klein, A.; Budnikova, Y. H.; Sinyashin, O. G. J. Organomet. Chem. 2007, 692, 3156-3166.
49. III intermediates in Ni-catalyzed Negishi reactions
50. see: Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680-3688.
51. Phapale, V. B.; Buñuel, E.; Garc?́a-Iglesias, M.; Cárdenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790-8795.
52. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175-13813.