Ligand-controlled regiodivergent Ni-catalyzed reductive carboxylation of allyl esters with CO2

Journal of the American Chemical Society

Volumn 136, Issue 51, 2014, Pages 17702-17705

  Moragas, Toni ^a   Cornella, Josep ^a   Martin, Ruben ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CARBOXYLATION; CATALYSIS; ESTERS; LIGANDS;

ALLYL ESTERS; SIMPLE METHOD; USER FRIENDLY;

NICKEL COMPOUNDS;

ALLYL COMPOUND; CARBON DIOXIDE; ESTER DERIVATIVE; LIGAND;

ARTICLE; CARBOXYLATION; CATALYST; CONTROLLED STUDY; CYCLIZATION; ISOMER; NUCLEOPHILICITY;

EID: 84919941481     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja509077a     Document Type: Article

References (51)

1. Diederich, F.; de Meijere, A., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
2. Mahatthananchai, J.; Dumas, A. M.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 10954
3. Afagh, N. A.; Yudin, A. K. Angew. Chem., Int. Ed. 2010, 49, 262
4. Trost, B. M. Science 1983, 219, 245
5. Arnold, J. S.; Zhang, Q.; Nguyen, H. M. Eur. J. Org. Chem. 2014, 23, 4925
6. Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467
7. Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675
8. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921
9. Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242
10. Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299
11. Everson, D. A.; Weix, D. J. J. Org. Chem. 2014, 79, 4793
12. Knappe, C. E. I.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828
13. Tan, Z.; Wan, X.; Zang, Z.; Qian, Q.; Deng, W.; Gong, H. Chem. Commun. 2014, 50, 3827
14. Anka-Lufford, L. L.; Prinsel, M. R.; Weix, D. J. J. Org. Chem. 2012, 77, 9989
15. Wang, S.; Qian, Q.; Gong, H. Org. Lett. 2012, 14, 3352
16. Durandetti, M.; Nedelec, J.-Y.; Perichon, J. J. Org. Chem. 1996, 61, 1748
17. Zhang, L.; Hou, Z. Chem. Sci. 2013, 4, 3395
18. Tsuji, Y.; Fujihara, T. Chem. Commun. 2012, 48, 9956
19. Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kuhn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510
20. Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435
21. Martin, R.; Kleij, A. W. ChemSusChem 2011, 4, 1259
22. Liu, Y.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 11212
23. Correa, A.; Leon, T.; Martin, R. J. Am. Chem. Soc. 2014, 136, 1062
24. Leon, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221
25. Correa, A.; Martin, R. J. Am. Chem. Soc. 2009, 131, 15974
26. Nogi, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Chem. Commun. 2014, 50, 13052
27. Tran-Vu, H.; Daugulis, O. ACS Catal. 2013, 3, 2417
28. Fujihara, T.; Nogi, K.; Xu, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 9106
29. Maag, H. Prodrugs of Carboxylic Acids; Springer: New York, 2007.
30. Zhao, Y.; Weix, D. J. J. Am. Chem. Soc. 2014, 136, 48
31. Köpfer, A.; Sam, B.; Breit, B.; Krische, M. J. Chem. Sci. 2013, 4, 1876
32. Shareef, A.-R.; Sherman, D. H.; Montgomery, J. Chem. Sci. 2012, 3, 892
33. Miller, K. M.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 15342
34. Tani, Y.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2014, 10.1021/ja512040c
35. Duong, H. A.; Huleatt, P. B.; Tan, Q.-W.; Shuying, E. L. Org. Lett. 2013, 15, 4034
36. Hruszkewycz, D. P.; Wu, J.; Hazari, N.; Incarvito, C. D. J. Am. Chem. Soc. 2011, 133, 3280
37. Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057
38. Wu, J.; Green, J. C.; Hazari, N.; Hruszkewycz, D. P.; Incarvito, C. D.; Schmeier, T. J. Organometallics 2010, 29, 6369
39. Miao, B.; Ma, S. Chem. Commun. 2014, 50, 3285
40. Hung, T.; Jolly, P. W.; Wilke, G. J. Organomet. Chem. 1980, 190, C5
41. Courtois, G.; Migniac, L. J. Organomet. Chem. 1974, 69, 1
42. Friederich, L. E.; Cormier, R. A. J. Org. Chem. 1971, 36, 3011
43. Wu, F.; Lu, W.; Qian, Q.; Ren, Q.; Gong, H. Org. Lett. 2012, 14, 3044
44. Metzger, A.; Bernhardt, S.; Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed. 2010, 49, 4665
45. Luo, L.; Zhang, J.-J.; Ling, W.-J.; Shao, Y.-L.; Wang, Y.-W.; Peng, Y. Synthesis 2014, 46, 1908
46. Yang, D.; Belardi, J. K.; Micalizio, G. C. Tetrahedron Lett. 2011, 52, 2144
47. Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 10.1021/ja510653n
48. Powers, D. C.; Anderson, B. L.; Nocera, D. G. J. Am. Chem. Soc. 2013, 135, 18876
49. Taking into consideration the tetrahedral geometry for Ni(0) complexes, the square-planar environment found for 5 might suggest that this complex would be best described as a Ni(II) complex of a reduced quaterpyridine ligand dianion or a Ni(I)- L5 with an antiferromagnetic coupling. For an excellent review dealing with redox-active ligands, see: Hu, X. Chem. Sci. 2011, 2, 1867
50. Suh, H.-W.; Guard, L. M.; Hazari, N. Chem. Sci. 2014, 5, 3859
51. Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2008, 130, 15254