Pd(OAc)2-catalyzed alkoxylation of arylnitriles via sp 2 C-H bond activation using cyano as the directing group

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 8362-8366

  Li, Wu ^a   Sun, Peipei ^a,b  

^a NANJING NORMAL UNIVERSITY   (China)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYLATION; C-H BOND; CH-BOND ACTIVATION; ELECTRON-DONATING GROUP; ELECTRONWITHDRAWING; FUNCTIONALIZED; OPTIMAL REACTION CONDITION; REACTION TEMPERATURE;

CHEMISTRY; ORGANIC COMPOUNDS;

CATALYSIS;

ARYLNITRILE; NITRILE; PALLADIUM ACETATE; UNCLASSIFIED DRUG;

ALKOXYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON; REACTION TEMPERATURE; TEMPERATURE;

CATALYSIS; HYDROGEN BONDING; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION; PALLADIUM;

EID: 84868143895     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301384r     Document Type: Article

References (50)

1. For partial recent reviews, see: (a) Bergman, R. G. Nature 2007, 446, 391
2. (b) Daugulis, O.; Do, H. Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
3. (c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
4. (d) Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2010, 111, 1293.
5. (e) Yu, J. Q.; Shi, Z. J. In Top. Curr. Chem.; Daugulis, O., Eds.; Springer-Verlag: Berlin, 2010; Vol. 292, pp 57-84
6. (f) Liu, C.; Zhang, H.; Shi, W.; Lei, A. W. Chem. Rev. 2011, 111, 1780
7. (g) Davies, H. L.; Bois, J. D.; Yu, J. Q. Chem. Soc. Rev. 2011, 40, 1855.
8. (a) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586
9. (b) Yang, S. D.; Li, B. J.; Wan, X. B.; Shi, Z. J. J. Am. Chem. Soc. 2007, 129, 6066
10. (c) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300
11. (d) Chen, X.; Li, J. J.; Hao, X. S.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc. 2006, 128, 78.
12. (e) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
13. Engle, K. M.; Mei, T. S.; Wasa, M.; Yu, J. Q. Acc. Chem. Res. 2012, 45, 788.
14. (a) Giri, R.; Maugel, N.; Li, J. J.; Wang, D. Q.; Breazzano, S. P.; Saunders, L. B.; Yu, J. Q. J. Am. Chem. Soc. 2007, 129, 3510.
15. (b) Zhang, X, G.; Dai, H, X.; Wasa, M.; Yu, J. Q. J. Am. Chem. Soc. 2012, 134, 11948
16. (c) Lu, Y.; Leow, D.; Wang, X. S.; Engle, K. M.; Yu, J. Q. Chem. Sci 2011, 2, 967
17. (d) Wang, X.; Lu, Y.; Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2010, 132, 12203
18. (e) Gandeepan, P.; Parthasarathy, K.; Cheng, C. H. J. Am. Chem. Soc. 2010, 132, 8569.
19. (a) Rappoport, Z. The Chemistry of the Cyano Group; Interscience Publishers: London, 1970
20. (b) Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; VCH: New York, 1989
21. (c) Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049.
22. Li, W.; Xu, Z. P.; Sun, P. P.; Jiang, X. Q.; Fang, M. Org. Lett. 2011, 13, 1286.
23. Leow, D.; Li, G.; Mei, T. S.; Yu, J. Q. Nature 2012, 486, 518.
24. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
25. Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451.
26. (a) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180
27. (b) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300
28. (c) Chen, M. S.; Prabagaran, N.; Labenz, N. A.; White, M. C. J. Am. Chem. Soc. 2005, 127, 6970
29. (d) Giri, R.; Liang, J.; Lei, J. G.; Li, J. J.; Wang, D. H.; Chen, X.; Naggar, I. C.; Guo, C.; Foxman, B. M.; Yu, J. Q. Angew. Chem ., Int. Ed. 2005, 44, 7420.
30. (e) Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285
31. (f) Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302.
32. (g) Powers, D. C.; Xiao, D. Y.; Geibel, M. A. L.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 14530
33. (h) Vickers, C. J.; Mei, T. S.; Yu, J. Q. Org. Lett. 2010, 12, 2511
34. (i) Gulevich, A. V.; Melkonyan, F. S.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 5528
35. (j) Vedernikov, A. N. Acc. Chem. Res. 2012, 45, 803.
36. (a) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141
37. (b) Wang, G. W.; Yuan, T. T. J. Org. Chem. 2010, 75, 476.
38. (c) Zhang, S. Y.; He, G.; Zhao, Y. S.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313.
39. Gandeepan, P.; Cheng, C. H. J. Am. Chem. Soc. 2012, 134, 5738.
40. For some involvement of PdIV intermediates in C-H functionalization reactions, also see: (a) Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A: Chem. 1996, 108, 35
41. (b) Wang, X.; Lu, Y.; Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2010, 132, 12203
42. (c) Engle, K. M.; Mei, T. S.; Wang, X.; Yu, J. Q. Angew. Chem., Int. Ed. 2011, 50, 1478.
43. (d) Karthikeyan, J.; Cheng, C. H. Angew. Chem., Int. Ed. 2011, 50, 9880.
44. Kim, J.; Choi, J.; Shin, K.; Chang, S. J. Am. Chem. Soc. 2012, 134, 2528.
45. Bennetau, B.; Rajarison, F.; Dunoguts, J. Tetrahedron. 1993, 49, 10843.
46. Robertson, A.; Robinson, R. J. Chem. Soc. 1927, 2196.
47. Ugi, I.; Fetzer, U.; Eholzer, U.; Knupfer, H.; Offermann, K. Angew. Chem. 1965, 77, 492.
48. Bradsher, C. K.; Brown, F. C.; Porter, H. K. J. Am. Chem. Soc. 1954, 76, 2357.
49. Sellstetd, J. H.; Guinosso, C. J.; Begany, A. J.; Bell, S. C.; Rosenthale, M. J. Med. Chem. 1972, 15, 865.
50. Fisher, L. E.; Muchowski, J. M.; Clark, R. D. J. Org. Chem. 1992, 57, 2700.