Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2

Journal of the American Chemical Society

Volumn 138, Issue 24, 2016, Pages 7504-7507

  Börjesson, Marino ^a   Moragas, Toni ^a   Martin, Ruben ^a,b  

^a BARCELONA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Spain)

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

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC PRESSURE; CARBOXYLATION; CHLORINE COMPOUNDS;

ALKYL CHLORIDES; CATALYTIC CARBOXYLATION; CROSS-COUPLINGS; ELECTROPHILES;

CARBON DIOXIDE;

ALKYL GROUP; CARBON DIOXIDE; CHLORIDE; ELECTROPHILE; NICKEL; PHENANTHROLINE; UNACTIVATED ALKYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CARBOXYLATION; CATALYST; CONTROLLED STUDY; COVALENT BOND; CROSS COUPLING REACTION; CYCLIZATION; DIASTEREOISOMER; ELECTRON TRANSPORT; X RAY CRYSTALLOGRAPHY;

EID: 84975815205     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b04088     Document Type: Article

References (55)

1. Gu, J.; Wang, X.; Xue, W.; Gong, H. Org. Chem. Front. 2015, 2, 1411 10.1039/C5QO00224A
2. Weix, D. J. Acc. Chem. Res. 2015, 48, 1767 10.1021/acs.accounts.5b00057
3. Moragas, T.; Correa, A.; Martin, R. Chem.-Eur. J. 2014, 20, 8242 10.1002/chem.201402509
4. Knappke, C. E. I.; Grupe, S.; Gärtner, D.; Corpet, M.; Gosmini, C.; Jacobi von Wangelin, A. Chem.-Eur. J. 2014, 20, 6828 10.1002/chem.201402302
5. Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299 10.1038/nature13274
6. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Meijere, A., Eds.; Wiley-VCH: Weinheim, 2004.
7. Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937 10.1039/c1cs15129k
8. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417 10.1021/cr100327p
9. For a single example of a reductive homodimerization of an unactivated alkyl chloride: Prinsell, M.; Everson, D.; Weix, D. J. Chem. Commun. 2010, 46, 5743 10.1039/c0cc01716g
10. For a recent intramolecular ring contraction: Tollefson, E. J.; Erickson, E. W.; Jarvo, E. R. J. Am. Chem. Soc. 2015, 137, 9760 10.1021/jacs.5b03870
11. Atack, T. C.; Cook, S. P. J. Am. Chem. Soc. 2016, 138, 6139 10.1021/jacs.6b03157
12. Lu, Z.; Fu, G. C. Angew. Chem., Int. Ed. 2010, 49, 6676 and references therein 10.1002/anie.201003272
13. Rossi, R.; Bellina, F.; Lessi, M. Tetrahedron 2011, 67, 6969 10.1016/j.tet.2011.06.001
14. Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036 10.1039/b611177g
15. Zhang, L.; Hou, Z. Chem. Sci. 2013, 4, 3395 10.1039/c3sc51070k
16. Tsuji, Y.; Fujihara, T. Chem. Commun. 2012, 48, 9956 10.1039/c2cc33848c
17. Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kuhn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510 10.1002/anie.201102010
18. Huang, K.; Sun, C.-L.; Shi, Z.-J. Chem. Soc. Rev. 2011, 40, 2435 10.1039/c0cs00129e
19. Martin, R.; Kleij, A. W. ChemSusChem 2011, 4, 1259 10.1002/cssc.201100102
20. Patai, S. The Chemistry of Acid Derivatives; Wiley: New York, 1992.
21. Goossen, L. J.; Rodríguez, N.; Goosen, K. Angew. Chem., Int. Ed. 2008, 47, 3100 10.1002/anie.200704782
22. Maag, H. Prodrugs of Carboxylic Acids; Springer: New York, 2007.
23. Osakada, K.; Sato, R.; Yamamoto, T. Organometallics 1994, 13, 4645 10.1021/om00023a078
24. Moragas, T.; Gaydou, M.; Martin, R. Angew. Chem., Int. Ed. 2016, 55, 5053 10.1002/anie.201600697
25. Wang, X.; Nakajima, M.; Martin, R. J. Am. Chem. Soc. 2015, 137, 8924 10.1021/jacs.5b05513
26. Wang, X.; Liu, Y.; Martin, R. J. Am. Chem. Soc. 2015, 137, 6476 10.1021/jacs.5b03340
27. Moragas, T.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 17702 10.1021/ja509077a
28. Liu, Y.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 11212 10.1021/ja5064586
29. Rebih, F.; Andreini, M.; Moncomble, A.; Harrison-Marchand, A.; Maddaluno, J.; Durandetti, M. Chem.-Eur. J. 2016, 22, 3758 10.1002/chem.201503926
30. Nogi, K.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Org. Chem. 2015, 80, 11618 10.1021/acs.joc.5b02307
31. Mita, T.; Higuchi, Y.; Sato, Y. Chem.-Eur. J. 2015, 21, 16391 10.1002/chem.201503359
32. Nogi, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Chem. Commun. 2014, 50, 13052 10.1039/C4CC03644A
33. Tran-Vu, H.; Daugulis, O. ACS Catal. 2013, 3, 2417 10.1021/cs400443p
34. Fujihara, T.; Nogi, K.; Xu, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 9106 10.1021/ja303514b
35. Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80 and ref 11f 10.1246/bcsj.63.80
36. Tobisu, M.; Chatani, N. Acc. Chem. Res. 2015, 48, 1717 10.1021/acs.accounts.5b00051
37. Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081 10.1039/C4CS00206G
38. Yamaguchi, J.; Muto, K.; Itami, K. Eur. J. Org. Chem. 2013, 2013, 19 10.1002/ejoc.201200914
39. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Perce, V. Chem. Rev. 2011, 111, 1346 10.1021/cr100259t
40. Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486 10.1021/ar100082d
41. 2)-O electrophiles have shown to be suited for catalytic reductive carboxylation techniques: Correa, A.; León, T.; Martin, R. J. Am. Chem. Soc. 2014, 136, 1062 10.1021/ja410883p
42. Wang, X.; Wang, S.; Xue, W.; Gong, H. J. Am. Chem. Soc. 2015, 137, 11562 10.1021/jacs.5b06255
43. Zhao, C.; Jia, X.; Wang, X.; Gong, H. J. Am. Chem. Soc. 2014, 136, 17645 10.1021/ja510653n
44. Fressigne, C.; Girard, A.-L.; Durandetti, M.; Maddaluno, J. Angew. Chem., Int. Ed. 2008, 47, 891 10.1002/anie.200704139
45. Simaan, S.; Marek, I. Org. Lett. 2007, 9, 2569 and references therein 10.1021/ol070974x
46. Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073 10.1021/ja1073799
47. Biscoe, M. R.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 6686 10.1021/ja801137k
48. Laskowski, C. A.; Bungum, D. J.; Baldwin, S. M.; Del Ciello, S. A.; Iluc, V. M.; Hillhouse, G. L. J. Am. Chem. Soc. 2013, 135, 18272 10.1021/ja4095236
49. Breitenfeld, J.; Ruiz, J.; Wodrich, M. D.; Hu, X. J. Am. Chem. Soc. 2013, 135, 12004 10.1021/ja4051923
50. Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192 and references therein 10.1021/ja407589e
51. Cornella, J.; Gomez-Bengoa, E.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1997 10.1021/ja311940s
52. Velian, A.; Lin, S.; Miller, A. J. M.; Day, M. W.; Agapie, T. J. Am. Chem. Soc. 2010, 132, 6296 10.1021/ja101699a
53. Phapale, V. B.; Bunuel, E.; García-Iglesias, M.; Cardenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790 10.1002/anie.200702528
54. 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 10.1021/ja063334i
55. 2: Menges, F. S.; Craig, S. M.; Tötsch, N.; Bloomfield, A.; Ghosh, S.; Krüger, H.-J.; Johnson, M. A. Angew. Chem., Int. Ed. 2016, 55, 1282 10.1002/anie.201507965