Late-Stage Diversification of Peptides by Metal-Free C-H Arylation

Chemistry - A European Journal

Volumn 20, Issue 41, 2014, Pages 13099-13102

  Zhu, Yingjun ^a   Bauer, Michaela ^a   Ploog, Jasper ^a   Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

C H activation; chemoselective reactions; late stage diversification; metal free reactions; peptides

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CHEMICAL REACTIONS; PEPTIDES; POLYCYCLIC AROMATIC HYDROCARBONS;

C-H ACTIVATION; CHEMOSELECTIVE REACTIONS; FUNCTIONALIZED; INDOLE DERIVATIVES; LATE STAGE; METAL-FREE REACTIONS; MILD REACTION CONDITIONS; SITE SELECTIVE;

METALS;

EID: 84941054992     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404603     Document Type: Article

References (43)

1. J. He, S. Li, Y. Deng, H. Fu, B. N. Laforteza, J. E. Spangler, A. Homs, J.-Q. Yu, Science 2014, 343, 1216-1220.
2. J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369-375.
3. L.-S. Zhang, G. Chen, X. Wang, Q.-Y. Guo, X.-S. Zhang, F. Pan, K. Chen, Z.-J. Shi, Angew. Chem. 2014, 126, 3980-3984;
4. Angew. Chem. Int. Ed. 2014, 53, 3899-3903.
5. K. Godula, D. Sames, Science 2006, 312, 67-72.
6. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092-9142;
7. Angew. Chem. Int. Ed. 2012, 51, 8960-9009.
8. Y. Takaoka, A. Ojida, I. Hamachi, Angew. Chem. 2013, 125, 4182-4200;
9. Angew. Chem. Int. Ed. 2013, 52, 4088-4106.
10. E. M. Sletten, C. R. Bertozzi, Angew. Chem. 2009, 121, 7108-7133;
11. Angew. Chem. Int. Ed. 2009, 48, 6974-6998.
12. C. P. R. Hackenberger, D. Schwarzer, Angew. Chem. 2008, 120, 10182-10228;
13. Angew. Chem. Int. Ed. 2008, 47, 10030-10074.
14. L. S. Witus, M. B. Francis, Acc. Chem. Res. 2011, 44, 774-783.
15. S. H. Weisbrod, A. Marx, Chem. Commun. 2008, 5675-5685.
16. H. C. Hang, C. Yu, D. L. Kato, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2003, 100, 14846-14851.
17. R. K. V. Lim, Q. Lin, Chem. Commun. 2010, 46, 1589-1600.
18. J. M. Chalker, G. J. L. Bernardes, B. G. Davis, Acc. Chem. Res. 2011, 44, 730-741.
19. Selected recent example:, Z. Gao, V. Gouverneur, B. G. Davis, J. Am. Chem. Soc. 2013, 135, 13612-13615.
20. For a further recent representative example, see:, A. C. Obermeyer, J. B. Jarman, C. Netirojjanakul, C. El Muslemeany, M. B. Francis, Angew. Chem. 2014, 126, 1075-1079;
21. Angew. Chem. Int. Ed. 2014, 53, 1057-1061, and references therein.
22. L. Ackermann, Pure Appl. Chem. 2010, 82, 1403-1413;
23. L. Ackermann, Acc. Chem. Res. 2014, 47, 281-295.
24. For recent reviews on metal-catalyzed C-H activations, see:
25. S. A. Girard, T. Knauber, C.-J. Li, Angew. Chem. Int. Ed. 2014, 53, 74-100;
26. S. De Sarkar, W. Liu, S. I. Kozhushkov, L. Ackermann, Adv. Synth. Catal. 2014, 356, 1461-1479;
27. N. Kuhl, M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382-10401;
28. Angew. Chem. Int. Ed. 2012, 51, 10236-10254;
29. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788-802;
30. R. G. Bergman, Nature 2007, 446, 391-393; and references therein. For recent examples with precious palladium complexes, see:
31. T. J. Williams, A. J. Reay, A. C. Whitwood, I. J. S. Fairlamb, Chem. Commun. 2014, 50, 3052-3054;
32. J. Ruiz-Rodríguez, F. Albericio, R. Lavilla, Chem. Eur. J. 2010, 16, 1124-1127;
33. H. K. Potukuchi, T. Bach, J. Org. Chem. 2013, 78, 12263-12267.
34. L. Ackermann, M. Dell′Acqua, S. Fenner, R. Vicente, R. Sandmann, Org. Lett. 2011, 13, 2358-2360.
35. V. V. Zhdankin, Hypervalent Iodine Chemistry: Preparation, Structure and Synthetic Applications of Polyvalent Iodine Compounds, Wiley, Chichester, 2014.
36. For, a recent review on hypervalent iodine reagents:, E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214-9234;
37. Angew. Chem. Int. Ed. 2009, 48, 9052-9070.
38. For detailed information, see the Supporting Information.
39. A recent example:
40. T. Dohi, M. Ito, N. Yamaoka, K. Morimoto, H. Fujioka, Y. Kita, Angew. Chem. 2010, 122, 3406-3409;
41. Angew. Chem. Int. Ed. 2010, 49, 3334-3337.
42. Reactions with ortho-but-3-enylaryl-substituted iodonium salts did not give rise to any radical cyclization products.
43. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740-4761.