Merging photoredox and nickel catalysis: Decarboxylative cross-coupling of carboxylic acids with vinyl halides

Journal of the American Chemical Society

Volumn 137, Issue 2, 2015, Pages 624-627

  Noble, Adam ^a   McCarver, Stefan J ^a   Macmillan, David W C ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; CATALYSIS; CHEMICAL REACTIONS; NICKEL;

ALKYL CARBOXYLIC ACIDS; ALPHA-AMINO ACIDS; CROSS-COUPLINGS; HIGH-EFFICIENCY; NICKEL CATALYSIS; SIMPLE REACTION; VINYL HALIDES; VINYL IODIDES;

MERGING;

ALKYL GROUP; ALPHA AMINO ACID; AMINO ACID; BROMIDE; CARBOXYLIC ACID; HALIDE; HYDROCARBON; IODIDE; NICKEL; VINYL DERIVATIVE; VINYL BROMIDE; VINYL IODIDE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CROSS COUPLING REACTION; DECARBOXYLATION; DIASTEREOISOMER; ELECTRON TRANSPORT; OXIDATION REDUCTION POTENTIAL; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

CARBOXYLIC ACIDS; CATALYSIS; NICKEL; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; VINYL COMPOUNDS;

EID: 84921483701     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja511913h     Document Type: Article

References (53)

1. van Santen, R. A. In Catalysis: From Principles to Applications, 1 st ed.; Beller, M., Renken, A., van Santen, R. A., Eds.; Wiley-VCH: Weinheim, 2012; p 3.
2. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
3. Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
4. Godula, K.; Sames, D. Science 2006, 312, 67
5. Baudoin, O. Angew. Chem., Int. Ed. 2007, 46, 1373
6. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
7. Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
8. Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030
9. Gooßen, L. J.; Gooßen, K. In Topics in Organometallic Chemistry, Vol. 44; Gooßen, L. J., Ed.; Springer-Verlag: Berlin, 2013; p 121.
10. Park, K.; Lee, S. RSC Adv. 2013, 3, 14165
11. Shang, R.; Yang, Z.-W.; Wang, Y.; Zhang, S.-L.; Liu, L. J. Am. Chem. Soc. 2010, 132, 14391
12. Shang, R.; Huang, Z.; Chu, L.; Fu, Y.; Liu, L. Org. Lett. 2011, 13, 4240
13. Xu, Z.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2013, 52, 3272
14. Chou, C.-M.; Chatterjee, I.; Studer, A. Angew. Chem., Int. Ed. 2011, 50, 8614
15. Yeung, P. Y.; Chung, K. H.; Kwong, F. Y. Org. Lett. 2011, 13, 2912
16. Shang, R.; Ji, D.-S.; Chu, L.; Fu, Y.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 4470
17. Feng, Y.-S.; Wu, W.; Xu, Z.-Q.; Li, Y.; Li, M.; Xu, H.-J. Tetrahedron 2012, 68, 2113
18. Bi, H.-P.; Chen, W.-W.; Liang, Y.-M.; Li, C.-J. Org. Lett. 2009, 11, 3246
19. Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 1798
20. Bi, H.-P.; Qingfeng, T.; Guan, M.; Chen, W.-W.; Liang, Y.-M.; Yao, X.; Li, C.-J. J. Org. Chem. 2010, 75, 783
21. Wang, Y.; Zhang, L.; Yang, Y.; Zhang, P.; Du, Z.; Wang, C. J. Am. Chem. Soc. 2013, 135, 18048
22. Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401
23. Wang, Z.; Zhu, L.; Yin, F.; Su, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 4258
24. Liu, X.; Wang, Z.; Cheng, X.; Li, C. J. Am. Chem. Soc. 2012, 134, 14330
25. Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2011, 3, 633
26. Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257
27. Chu, L.; Ohta, C.; Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 10886
28. Noble, A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 11602
29. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617
30. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322
31. Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36
32. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985
33. Osawa, M.; Nagai, H.; Akita, M. Dalton Trans. 2007, 827
34. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566
35. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034
36. Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Chem.-Eur. J. 2012, 18, 5170
37. Sahoo, B.; Hopkinson, M. N.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 5505
38. Shu, X. Z.; Zhang, M.; He, Y.; Frei, H.; Toste, F. D. J. Am. Chem. Soc. 2014, 136, 5844
39. Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433
40. Xie, J.; Xu, P.; Li, H.; Xue, Q.; Jin, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5672
41. Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502
42. Pfister, K. F.; Grunberg, M. F.; Gooßen, L. J. Adv. Synth. Catal. 2014, 356, 3302
43. Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 6195
44. Lowry, M. S.; Goldsmith, J. I.; Slinker, J. D.; Rohl, R.; Pascal, R. A., Jr.; Malliaras, G. G.; Bernhard, S. Chem. Mater. 2005, 17, 5712
45. Andrieux, C. P.; Gonzalez, F.; Saveant, J. J. Electroanal. Chem. 2001, 498, 171
46. Galicia, M.; Gonzalez, F. J. J. Electrochem. Soc. 2002, 149, D46
47. Bockman, T. M.; Hubig, S. M.; Kochi, J. K. J. Org. Chem. 1997, 62, 2210
48. Durandetti, M.; Devaud, M.; Perichon, J. New J. Chem. 1996, 20, 659
49. Ladouceur, S.; Fortin, D.; Zysman-Colman, E. Inorg. Chem. 2011, 50, 11514
50. Devery, J. J., III; Douglas, J. J.; Nguyen, J. D.; Cole, K. P.; Flowers, R. A., II; Stephenson, C. R. J. Chem. Sci. 2015, 6, 537
51. Reference 11c.
52. Singh, K.; Staig, S. J.; Weaver, J. D. J. Am. Chem. Soc. 2014, 136, 5275
53. De Clerq, E. Nat. Rev. Drug Discovery 2002, 1, 13