Palladium-catalyzed N-nitroso-directed C-H alkoxylation of arenes and subsequent formation of 2-alkoxy-N-alkylarylamines

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9888-9893

  Gao, Tingting ^a   Sun, Peipei ^a  

^a NANJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS;

ALKOXYLATION; CHEMICAL EQUATIONS; N-ALKYLANILINES; NITROSO; PALLADIUM-CATALYZED; SECONDARY ALCOHOLS;

PALLADIUM;

ALCOHOL DERIVATIVE; AMINE; NITROSO DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; REAGENT; ALKOXYL RADICAL; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; OXIDIZING AGENT;

ALKOXYLATION; ARTICLE; CHEMICAL MODIFICATION; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; REDUCTION; STEREOSPECIFICITY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALCOHOLS; CATALYSIS; HYDROGEN BONDING; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; NITROSO COMPOUNDS; OXIDANTS; PALLADIUM;

EID: 84907978505     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501902d     Document Type: Article

References (39)

1. (a) Czarnik, A. W. Acc. Chem. Res. 1996, 29, 112.
2. (b) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451.
3. (c) Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.
4. (d) Elias, H. G. An Introduction to Polymer Science ; Wiley-VCH: Weinheim, 1997.
5. (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
6. (b) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 3395.
7. (c) Hartwig, J. H. Angew. Chem., Int. Ed. 1998, 37, 2046.
8. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
9. (e) Torraca, K. E.; Huang, X.; Parrich, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 10770.
10. (f) Gowrisankar, S.; Sergeev, A. G.; Anbarasan, P.; Spannenberg, A.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 11592.
11. (g) Wu, X.; Fors, B. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9943.
12. Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
13. Wang, G. W.; Yuan, T. T. J. Org. Chem. 2010, 75, 476.
14. Jiang, T. S.; Wang, G. W. J. Org. Chem. 2012, 77, 9504.
15. Zhang, S. Y.; He, G.; Zhao, Y. S.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313.
16. Li, W.; Sun, P. P. J. Org. Chem. 2012, 77, 8362.
17. Yin, Z. W.; Jiang, X. Q.; Sun, P. P. J. Org. Chem. 2013, 78, 10002.
18. Chen, F. J.; Zhao, S.; Hu, F.; Chen, K.; Zhang, Q.; Zhang, S. Q.; Shi, B. F. Chem. Sci. 2013, 4, 4187.
19. Zhang, C.; Sun, P. P. J. Org. Chem. 2014, 79, 8457.
20. Shi, S. P.; Kuang, C. X. J. Org. Chem. 2014, 79, 6105.
21. (a) Wang, X.; Lu, Y.; Dai, H. X.; Yu, J. Q. J. Am. Chem. Soc. 2010, 132, 12203.
22. (b) Wang, H.; Li, G.; Engle, K. M.; Yu, J. Q. J. Am. Chem. Soc. 2013, 135, 6774.
23. (c) Xiao, B.; Gong, T. J.; Liu, Z. J.; Liu, J. H.; Luo, D. F.; Xu, J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 9250.
24. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
25. (a) Challis, B. C.; Challis, J. A. N-Nitrosamines and N-nitrosoimines. In The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, U.K., 1982.
26. (b) Moncada, S.; Palmer, R. M. J.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109.
27. (c) Guo, Z. M.; Xian, M.; Zhang, W.; McGill, A.; Wang, P. G. Bioorg. Med. Chem. 2001, 9, 99.
28. (a) Lee, J.; Chen, L.; West, A. H.; Richter-Addo, G. B. Chem. Rev. 2002, 102, 1019.
29. (b) Hartman, W. W.; Roll, L. J. Org. Synth. 1933, 13, 82.
30. (a) Constable, A. G.; McDonald, W. S.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 2282.
31. (b) Xu, N.; Goodrich, L. E.; Lehnert, N.; Powell, D. R.; Richter-Addo, G. B. Inorg. Chem. 2010, 49, 4405.
32. Liu, B. Q.; Fan, Y.; Gao, Y.; Sun, C.; Xu, C.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 468.
33. Liu, B. Q.; Song, C.; Sun, C.; Zhou, S. G.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625.
34. Wang, C. M.; Huang, Y. Org. Lett. 2013, 15, 5294.
35. Xie, F.; Qi, Z. S.; Yu, S. J.; Li, X. W. J. Am. Chem. Soc. 2014, 136, 4780.
36. (a) Zani, L.; Eichhorn, T.; Bolm, C. Chem. - Eur. J. 2007, 13, 2587.
37. (b) Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477.
38. (c) Maiti, A.; Reddy, P. V. N.; Sturdy, M.; Marler, L.; Pegan, S. D.; Mesecar, A. D.; Pezzuto, J. M.; Cushman, M. J. Med. Chem. 2009, 52, 1873.
39. (d) Gangjee, A.; Zhao, Y.; Lin, L.; Raghavan, S.; Roberts, E. G.; Risinger, A. L.; Hamel, E.; Mooberry, S. L. J. Med. Chem. 2010, 53, 8116.