Palladium-catalyzed alkylation of unactivated C(sp3)-H bonds with primary alkyl iodides at room temperature: Facile synthesis of β-alkyl α-amino acids

Organic Chemistry Frontiers

Volumn 2, Issue 10, 2015, Pages 1318-1321

  Wang, B ^a   Wu, X ^a   Jiao, R ^a   Zhang, S Y ^a   A Nack, W ^a   He, G ^a   Chen, G ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; PALLADIUM;

ALKYL IODIDES; ALPHA-AMINO ACIDS; AMINOQUINOLINE; EFFICIENT PROTOCOLS; ELECTRON WITHDRAWING GROUP; FACILE SYNTHESIS; PALLADIUM-CATALYZED; REACTION CONDITIONS;

AMINO ACIDS;

EID: 84941798724     PISSN: 20524110     EISSN: 20524129     Source Type: Journal    
DOI: 10.1039/c5qo00112a     Document Type: Article

References (41)

1. For selected reviews on Pd-catalyzed C(sp3)-H functionalization: (a) X. Chen, K. M. Engle, D.-H. Wang and J.-Q. Yu, Angew. Chem., Int. Ed., 2009, 48, 5094;
2. (b) T. W. Lyons and M. S. Sanford, Chem. Rev., 2010, 110, 1147;
3. (c) R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer and O. Baudoin, Chem. - Eur. J., 2010, 16, 2654.
4. For selected reviews on C(sp3)-H for synthesis of complex molecules. (a) K. Godula and D. Sames, Science, 2006, 312, 67;
5. (b) H. M. Davies and J. R. Manning, Nature, 2008, 451, 417;
6. (c) W. R. Gutekunst and P. S. Baran, Chem. Soc. Rev., 2011, 40, 1976;
7. (d) L. McMurray, F. OHara and M. Gaunt, Chem. Soc. Rev., 2011, 40, 1885;
8. (e) J. Yamaguchi, A. D. Yamaguchi and K. Itami, Angew. Chem., Int. Ed., 2012, 51, 8960.
9. For selected reviews on metal-catalyzed C-H alkylations: (a) L. Ackermann, Chem. Commun., 2010, 46, 4866;
10. (b) D. A. Colby, A. S. Tsai, R. G. Bergman and J. A. Ellman, Acc. Chem. Res., 2012, 45, 814.
11. For selected reviews on metal-catalyzed cross coupling of alkyl halides: (a) A. C. Frisch and M. Beller, Angew. Chem., Int. Ed., 2005, 44, 674;
12. (b) A. Rudolph and M. Lautens, Angew. Chem., Int. Ed., 2009, 48, 2656;
13. (c) M. R. Netherton and G. C. Fu, Top. Organomet. Chem., 2005, 14, 85.
14. For selected examples of Pd-catalyzed C-H alkylations with alkyl halides: (a) S. J. Tremont and H. U. Rahmen, J. Am. Chem. Soc., 1984, 106, 5759;
15. (b) M. Catellani, F. Frignani and A. Rangoni, Angew. Chem., Int. Ed. Engl., 1997, 36, 119;
16. (c) C. Bressy, D. Alberico and M. Lautens, J. Am. Chem. Soc., 2005, 127, 13148;
17. (d) Y.-H. Zhang, B.-F. Shi and J.-Q. Yu, Angew. Chem., Int. Ed., 2009, 48, 609;
18. (e) D. Lapointe and K. Fagnou, Org. Lett., 2009, 11, 4160;
19. (f ) L. Jiao and T. Bach, J. Am. Chem. Soc., 2011, 133, 12990.
20. (a) V. G. Zaitsev, D. Shabashov and O. Daugulis, J. Am. Chem. Soc., 2005, 127, 13154;
21. (b) D. Shabashov and O. Daugulis, J. Am. Chem. Soc., 2010, 132, 3965;
22. (c) L. D. Tran and O. Daugulis, Angew. Chem., Int. Ed., 2012, 51, 5188;
23. (d) E. T. Nadres, G. I. F. Santos, D. Shabashov and O. Daugulis, J. Org. Chem., 2013, 78, 9689.
24. (a) Y. Zhao and G. Chen, Org. Lett., 2011, 13, 4850;
25. (b) S.-Y. Zhang, G. He, W. A. Nack, Y.-S. Zhao, Q. Li and G. Chen, J. Am. Chem. Soc., 2013, 135, 2124;
26. (c) S.-Y. Zhang, Q. Li, G. He, W. A. Nack and G. Chen, J. Am. Chem. Soc., 2013, 135, 12135;
27. (d) G. He, S.-Y. Zhang, W. A. Nack, Q. Li and G. Chen, Angew. Chem., Int. Ed., 2013, 52, 11124;
28. (e) S.-Y. Zhang, Q. Li, G. He, W. A. Nack and G. Chen, J. Am. Chem. Soc., 2015, 137, 531.
29. (a) K. Chen, F. Hu, S.-Q. Zhang and B.-F. Shi, Chem. Sci., 2013, 4, 3906;
30. (b) K. Chen and B.-F. Shi, Angew. Chem., Int. Ed., 2014, 53, 11950.
31. For reports on AQ-directed Fe-catalyzed C-H alkylation with alkyl halides: (a) S. Asako, L. Ilies and E. Nakamura, J. Am. Chem. Soc., 2013, 135, 17755;
32. (b) L. Ilies, T. Matsubara, S. Ichikawa, S. Asako and E. Nakamura, J. Am. Chem. Soc., 2014, 136, 13126;
33. (c) E. R. Fruchey, B.M. Monks and S. P. Cook, J. Am. Chem. Soc., 2014, 136, 13130.
34. For reports on AQ-directed Ni-catalyzed C-H alkylation with alkyl halides: (a) Y. Aihara and N. Chatani, J. Am. Chem. Soc., 2013, 135, 5308;
35. (b) X. Wu, Y. Zhao and H. Ge, J. Am. Chem. Soc., 2014, 136, 1789;
36. (c) W. Song, S. Lackner and L. Ackermann, Angew. Chem., Int. Ed., 2014, 53, 2477.
37. G. Rouquet and N. Chatani, Angew. Chem., Int. Ed., 2013, 52, 11726.
38. (a) B. Wang, W. A. Nack, G. He, S.-Y. Zhang and G. Chen, Chem. Sci., 2014, 5, 3592;
39. (b) B. Wang, C. Lu, S.-Y. Zhang, G. He, W. A. Nack and G. Chen, Org. Lett., 2014, 16, 6260.
40. L. K. Mahal, K. J. Yarema and C. R. Bertozzi, Science, 1997, 276, 1125. αAAs bearing a ketone functional group are valuable tools for orthogonal labelling of peptides in chemical biology.
41. Removal of the Phth group of 50 would give L-2-amino-4-phosphonobutyric acid (L-AP4), a highly potent group III mGluR agonist. C. Selvam, C. Goudet, N. Oueslati, J.-P. Pin and F. Acher, J. Med. Chem., 2007, 50, 4656.