Purinyl N1-directed aromatic C-H oxidation in 6-arylpurines and 6-arylpurine nucleosides

Journal of Organic Chemistry

Volumn 78, Issue 15, 2013, Pages 7423-7435

  Chamala, Raghu Ram ^a   Parrish, Damon ^b   Pradhan, Padmanava ^a   Lakshman, Mahesh K ^a  

^a CITY COLLEGE OF NEW YORK   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CH-BOND ACTIVATION; DEOXYRIBONUCLEOSIDES; GLYCOSIDIC BOND; NITROGEN ATOM; OXIDIZATION; PALLADIUM-CATALYZED; REACTION CONDITIONS; X-RAY STRUCTURE;

CHEMICAL BONDS; ORGANOMETALLICS; PALLADIUM;

BIOMOLECULES;

AROMATIC COMPOUND; DEOXYRIBONUCLEOSIDE; NITROGEN; NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; CRYSTALLOGRAPHY; DEACETYLATION; HYDROLYSIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84881250119     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4008282     Document Type: Article

References (73)

1. Herdewijn, P., Ed. Modified Nucleosides in Biochemistry, Biotechnology and Medicine; Wiley-VCH: Weinheim, Germany, 2008.
2. Blackburn, G. M., Gait, M. J., Loakes, D., Williams, D. M., Eds. Nucleic Acids in Chemistry and Biology, 3 rd ed.; RSC Publishing: Cambridge, U.K., 2006.
3. Simons, C. Nucleoside Mimetics: Their Chemistry and Biological Properties; Gordon and Breach: Amsterdam, 2001.
4. Kisakürek, M. V., Rosemeyer, H., Eds. Perspectives in Nucleoside and Nucleic Acid Chemistry; Verlag Helvetica Chimica Acta and Wiley-VCH: Zürich, Switzerland, and Weinheim, Germany, 2000.
5. Suhadolnik, R. J. Nucleosides and Nucleic Acids as Biological Probes; Wiley: New York, 1979.
6. Handbook of C-H Transformations: Applications in Organic Synthesis; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Vols. 1 and 2.
7. Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, Germany, 1999; pp 47-79.
8. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802
9. Bugaut, X.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 7479-7481
10. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761
11. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
12. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
13. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824-889
14. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540-548
15. Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol 2011, 1, 191-206
16. You, S.-L.; Xia, J.-B. Top. Curr. Chem. 2010, 292, 165-194
17. Bellina, F.; Rossi, R. Tetrahedron 2009, 65, 10269-10310
18. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
19. Muñiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412-9423
20. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
21. Kulkarni, A. A.; Daugulis, O. Synthesis 2009, 4087-4109
22. McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447-2464
23. Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173-1193
24. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238
25. Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichim. Acta 2007, 40, 35-41
26. Kalyani, D.; Sanford, M. S. Top. Organomet. Chem. 2007, 24, 85-116
27. Yu, J.-Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041-4047
28. Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382-3388
29. Godula, K.; Sames, D. Science 2006, 312, 67-72
30. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469
31. Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514
32. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639
33. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932
34. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062-11087
35. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074-1086
36. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293-1314
37. Yoshikai, N. Synlett 2011, 1047-1051
38. Satoh, T.; Miura, M. Chem. Eur. J. 2010, 16, 11212-11222
39. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
40. Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013-1025
41. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879-5918
42. Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912-4924
43. Zhao, D.; Wang, W.; Yang, F.; Lan, J.; Yang, L.; Gao, G.; You, J. Angew. Chem., Int. Ed. 2009, 48, 3296-3300
44. Sahnoun, S.; Messaoudi, S.; Brion, J.-D.; Alami, M. Eur. J. Org. Chem. 2010, 6097-6102
45. Xi, P.; Yang, F.; Qin, S.; Zhao, D.; Lan, J.; Gao, G.; Hu, C.; You, J. J. Am. Chem. Soc. 2010, 132, 1822-1824
46. Sahnoun, S.; Messaoudi, S.; Peyrat, J.-F.; Brion, J.-D.; Alami, M. Tetrahedron Lett. 2008, 49, 7279-7283
47. Sahnoun, S.; Messaoudi, S.; Brion, J.-D.; Alami, M. Org. Biomol. Chem. 2009, 7, 4271-4278
48. Čerňa, I.; Pohl, R.; Hocek, M. Chem. Commun. 2007, 4729-4730
49. Storr, T. E.; Firth, A. G.; Wilson, K.; Darley, K.; Baumann, C. G.; Fairlamb, I. J. S. Tetrahedron 2008, 64, 6125-6137
50. Storr, T. E.; Baumann, C. G.; Thatcher, R. J.; De Ornellas, S.; Whitwood, A. C.; Fairlamb, I. J. S. J. Org. Chem. 2009, 74, 5810-5821
51. Guo, H.-M.; Jiang, L.-L.; Niu, H.-Y.; Rao, W.-H.; Liang, L.; Mao, R.-Z.; Li, D.-Y.; Qu, G.-R. Org. Lett. 2011, 13, 2008-2011
52. Lakshman, M. K.; Deb, A. C.; Chamala, R. R.; Pradhan, P.; Pratap, R. Angew. Chem., Int. Ed. 2011, 50, 11400-11404
53. Qu, G.-R.; Liang, L.; Niu, H.-Y.; Rao, W.-H.; Guo, H.-M.; Fossey, J. S. Org. Lett. 2012, 14, 4494-4497
54. Kim, J, Y.; Park, S. H.; Ryu, J.; Cho, S. H.; Kim, S. H.; Chang, S. J. Am. Chem. Soc. 2012, 134, 9110-9113
55. Guo, H.-M.; Rao, W.-H.; Niu, H.-Y.; Jiang, L.-L.; Meng, G.; Jin, J.-J.; Yang, X.-N.; Qu, G.-R. Chem. Commun. 2011, 47, 5608-5610
56. Čerňa, I.; Pohl, R.; Klepetářová, B.; Hocek, M. Org. Lett. 2006, 8, 5389-5392
57. Martín-Ortíz, M.; Gómez-Gallego, M.; Ramírez de Arellano, C.; Sierra, M. A. Chem. Eur. J. 2012, 18, 12603-12608
58. Henry, P. M. J. Org. Chem. 1971, 36, 1886-1890
59. Yoneyama, T.; Crabtree, R. H. J. Mol. Catal. A: Chem. 1996, 108, 35-40
60. Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301
61. Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790-12791
62. Racowski, J. M.; Dick, A. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 10974-10983
63. Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234-11241
64. Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302-309
65. Powers, D. C.; Geibel, M. A. L.; Klein, J. E. M. N.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050-17051
66. Powers, D. C.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Ritter, T. J. Am. Chem. Soc. 2010, 132, 14092-14103
67. Powers, D. C.; Ritter, T. Acc. Chem. Res. 2012, 45, 840-850
68. Powers, D. C.; Ritter, T. Top. Organomet. Chem. 2011, 35, 129-156
69. Yao, C. L.; He, L. P.; Korp, J. D.; Bear, J. L. Inorg. Chem. 1988, 27, 4389-4395
70. Bercaw, J. E.; Durrell, A. C.; Gray, H. B.; Green, J. C.; Hazari, N.; Labinger, J. A.; Winkler, J. R. Inorg. Chem. 2010, 49, 1801-1810
71. Powers, D. C.; Xiao, D. Y.; Geibel, M. A. L.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 14530-14536
72. Havelková, M.; Dvořák, D.; Hocek, M. Synthesis 2001, 1704-1710
73. Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779-7787