Electron-deficient olefin ligands enable generation of quaternary carbons by Ni-catalyzed cross-coupling

Journal of the American Chemical Society

Volumn 137, Issue 17, 2015, Pages 5638-5641

  Huang, Chung Yang ^a   Doyle, Abigail G ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; ELECTRONIC PROPERTIES; NICKEL; OLEFINS; ORGANIC COMPOUNDS;

C-C BOND FORMATION; CHEMO-SELECTIVITY; ELECTRON DEFICIENT OLEFINS; MODULAR FRAMEWORK; NEGISHI CROSS-COUPLING; PHENETHYLAMINES; QUATERNARY CARBON; REDUCTIVE ELIMINATION;

LIGANDS;

ALKENE; ANILINE DERIVATIVE; BETA SUBSTITUTED PHENETHYLAMINE DERIVATIVE; CARBON; NICKEL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRON;

EID: 84928955282     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02503     Document Type: Article

References (41)

1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
2. Organotransition Metal Chemistry, from Bonding to Catalysis; Hartwig, J. F., Ed.; University Science Books: New York, 2010.
3. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27
4. Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; García-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661
5. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
6. Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3350
7. Yamamoto, T.; Yamamoto, A.; Ikeda, S. J. Am. Chem. Soc. 1971, 93, 3360
8. Goliaszewski, A.; Schwartz, J. J. Am. Chem. Soc. 1984, 106, 5028
9. Kurosawa, H.; Emoto, M.; Urabe, A.; Miki, K.; Kasai, N. J. Am. Chem. Soc. 1985, 107, 8253
10. Giovannini, R.; Stüdemann, T.; Gaelle, D.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 2387
11. Giovannini, R.; Knochel, P. J. Am. Chem. Soc. 1998, 120, 11186
12. Giovannini, R.; Stüdemann, T.; Devasagayaraj, A.; Dussin, G.; Knochel, P. J. Org. Chem. 1999, 64, 3544
13. Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79
14. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840
15. Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525
16. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674
17. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
18. Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 9541
19. Nielsen, D. K.; Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 13605
20. Duda, M. L.; Michael, F. E. J. Am. Chem. Soc. 2013, 135, 18347
21. Takeda, Y.; Ikeda, Y.; Kuroda, A.; Tanaka, S.; Minakata, S. J. Am. Chem. Soc. 2014, 136, 8544
22. Jensen, K. L.; Standley, E. A.; Jamison, T. F. J. Am. Chem. Soc. 2014, 136, 11145
23. Huang, C.-Y.; Doyle, A. G. Chem. Rev. 2014, 114, 8153
24. Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 624
25. Tasker, S. Z.; Stanley, E. A.; Jamison, T. F. Nature 2014, 509, 299
26. Comprehensive Medicinal Chemistry; Taylor, J. B.; Triggle, D. J., Eds.; Pergamon Press: Oxford, 2007.
27. Drews, J. Science 2000, 287, 1960
28. Kalgutkar, A. S.; Jones, R.; Sawant, A. RSC Drug Discovery Series 2010, 1, 210
29. Chen, X.; Hussain, S.; Parveen, S.; Zhang, S.; Yang, Y.; Zhu, C. Curr. Med. Chem. 2012, 19, 3578
30. Scozzafava, A.; Carta, F.; Supuran, C. T. Expert Opin. Ther. Patents 2013, 23, 203
31. Shah, S. S. A.; Rivera, G.; Ashfaq, M. Mini-Rev. Med. Chem. 2013, 13, 70
32. McCann, L. C.; Organ, M. G. Angew. Chem., Int. Ed. 2014, 53, 4386 and references therein
33. Yadav, J. S.; Reddy, B. V. S.; Rao, R. S.; Veerendhar, G.; Nagaiah, K. Tetrahedron Lett. 2001, 42, 8067
34. Bera, M.; Roy, S. Tetrahedron Lett. 2007, 48, 7144
35. Bera, M.; Roy, S. J. Org. Chem. 2010, 75, 4402
36. Berry, M. D. J. Neurochem. 2004, 90, 257
37. Nichols, D. E. J. Pharm. Sci. 1981, 70, 839
38. Pellissier, H. Tetrahedron 2010, 66, 1509
39. Pellissier, H. Adv. Synth. Catal. 2014, 356, 1899
40. Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 5794
41. Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485