Palladium(II)-Catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines

Journal of the American Chemical Society

Volumn 137, Issue 5, 2015, Pages 2042-2046

  Chan, Kelvin S L ^a   Fu, Hai Yan ^a   Yu, Jin Quan ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; AMINO ACIDS; AROMATIC COMPOUNDS; CATALYSIS; CHEMICAL REACTIONS; PALLADIUM COMPOUNDS;

ARYL IODIDES; ARYLATIONS; C-H ARYLATION; CATALYTIC CYCLES; CYCLOPROPYL; DIASTEREO-SELECTIVITY; ENANTIOCONTROL; ENANTIOSELECTIVE;

ENANTIOSELECTIVITY;

AMINO ACID; CARBON; HYDROGEN; IODIDE; METHYLAMINE; PALLADIUM; AMINE; AROMATIC HYDROCARBON;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; SCALE UP; CHEMISTRY; STEREOISOMERISM;

AMINES; CATALYSIS; HYDROCARBONS, AROMATIC; PALLADIUM; STEREOISOMERISM;

EID: 84922767264     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512529e     Document Type: Article

References (32)

1. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438
2. Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483
3. Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem.-Eur. J. 2012, 18, 4480
4. Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238
5. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Chimia 2012, 66, 241
6. For an intermolecular example of enantioselective Pd(0)-catalyzed C(sp3)-H activation, see: Renaudat, A.; Jean-Gérard, L.; Jazzar, R.; Kefalidis, C. E.; Clot, E.; Baudoin, O. Angew. Chem., Int. Ed. 2010, 49, 7261
7. For an example of Pd-catalyzed atropselective arylation, see: Yamaguchi, K.; Yamaguchi, J.; Studer, A.; Itami, K. Chem. Sci. 2012, 3, 2165
8. Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882
9. Gao, D.-W.; Shi, Y.-C.; Gu, Q.; Zhao, Z.-L.; You, S.-L. J. Am. Chem. Soc. 2013, 135, 86
10. Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 132, 460
11. Pi, C.; Li, Y.; Cui, X.; Zhang, H.; Han, Y.; Wu, Y. Chem. Sci. 2013, 4, 2675
12. For an intermolecular example of enantioselective Pd(II)/MPAA-catalyzed C(sp2)-H activation and subsequent oxidation, see: Cheng, X.-F.; Li, Y.; Su, Y.-M.; Yin, F.; Wang, J.-Y.; Sheng, J.; Vora, H. U.; Wang, X.-S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 1236
13. For an intermolecular example of enantioselective Pd(II)/MPAA-catalyzed C(sp2)-H activation and subsequent iodination, see: Chu, L.; Wang, X.-C.; Moore, C. E.; Rheingold, A. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 16344
14. For an intermolecular example of enantioselective Pd(II)/MPAA-catalyzed cyclopropyl C-H activation and subsequent coupling with organoboron reagents, see: Wasa, M.; Engle, K. M.; Lin, D. W.; Yoo, E. J.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 19598
15. For an intermolecular example of enantioselective Pd(II)-catalyzed cyclobutyl C(sp3)-H activation and subsequent coupling with organoboron reagents using a MPAA analog (mono-protected amino- O -methylhydroxamic acid) ligand, see: Xiao, K.-J.; Lin, D. W.; Miura, M.; Zhu, R.-Y.; Gong, W.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 8138
16. For an example of Pd(II)/MPAA-catalyzed C(sp3)-H activation, see: Chan, K. S. L.; Wasa, M.; Chu, L.; Laforteza, B. N.; Miura, M.; Yu, J.-Q. Nat. Chem. 2014, 6, 146
17. Dyker, G. Angew. Chem., Int. Ed. 1994, 33, 103
18. Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
19. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824
20. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998.
21. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977
22. Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1
23. Denmark, S. E.; Beutner, G. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 85ff.
24. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911
25. Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919
26. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861
27. Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916
28. Zhu, S.; Cui, X.; Zhang, X. P. Eur. J. Inorg. Chem. 2012, 430
29. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
30. Powers, D. C.; Lee, E.; Ariafard, A.; Sanford, M. S.; Yates, B. F.; Canty, A. J.; Ritter, T. J. Am. Chem. Soc. 2012, 134, 12002
31. Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886
32. He, J.; Wasa, M.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 3387