Palladium-catalyzed unactivated c(sp3)-h bond activation and intramolecular amination of carboxamides: A new approach to β-lactams

Organic Letters

Volumn 16, Issue 2, 2014, Pages 480-483

  Sun, Wen Wu ^a,b   Cao, Pei ^a   Mei, Ren Qiang ^a   Li, Yue ^a   Ma, Yuan Liang ^a   Wu, Bin ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINOQUINOLINE DERIVATIVE; BETA LACTAM; BETA LACTAMASE; MK 8712; MONOBACTAM DERIVATIVE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; SYNTHESIS;

AMIDES; AMINATION; AMINOQUINOLINES; BETA-LACTAMASES; BETA-LACTAMS; CATALYSIS; MOLECULAR STRUCTURE; MONOBACTAMS; PALLADIUM;

EID: 84896778047     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403364k     Document Type: Article

References (42)

1. (a) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074
2. Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
3. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654.
4. (d) Wasa, M.; Engle, K. M.; Yu, J.-Q. Isr. J. Chem. 2010, 50, 605.
5. (e) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
6. (f) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902
7. McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885.
8. (h) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
9. Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896
10. Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
11. For reviews on construction of N-heterocycles by C-H functionalization, see: (a) Thansandote, P.; Lautens, M. Chem.-Eur. J. 2009, 15, 5874
12. Mei, T.-S.; Kou, L.; Ma, S.; Engle, K. M.; Yu, J.-Q. Synthesis 2012, 1778.
13. Selected examples for the synthesis of natural products through palladium-catalyzed C(sp3)-H functionalization: (a) Feng, Y.; Chen, G. Angew. Chem., Int. Ed. 2010, 49, 958
14. Gutekunst, W. R.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 19076
15. Gutekunst, W. R.; Gianatassio, R.; Baran, P. S. Angew. Chem., Int. Ed. 2012, 51, 7507.
16. Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058.
17. Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7.
18. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3.
19. Ye, X.; He, Z.; Ahmed, T.; Weise, K.; Akhmedov, N. G.; Petersen, J. L.; Shi, X. Chem. Sci. 2013, 4, 3712.
20. Zhang, Q.; Chen, K.; Rao, W.; Zhang, Y.; Chen, F.-J.; Shi, B.-F. Angew. Chem., Int. Ed. 2013, DOI: 10.1002/anie.201306625.
21. (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154
22. Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965
23. Tran, L. D.; Daugulis, O. Angew. Chem., Int. Ed. 2012, 51, 5188.
24. Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
25. (a) Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414
26. He, G.; Zhang, S.-Y.; Nack, W. A.; Li, Q.; Chen, G. Angew. Chem., Int. Ed. 2013, 52, 11124.
27. Ano, Y.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 12984.
28. Shang, R.; Ilies, L.; Matsumoto, A.; Nakamura, E. J. Am. Chem. Soc. 2013, 135, 6030.
29. Pan, F.; Shen, P.-X.; Zhang, L.-S.; Wang, X.; Shi, Z.-J. Org. Lett. 2013, 15, 4758.
30. Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
31. For review: Hartwig, J. F. Inorg. Chem. 2007, 46, 1936 and references cited therein.
32. A pioneering work by Daugulis9a showed that the arylation of 8-aminoquinoline-directed carboxamide 1 with 4′-iodoacetophenone afforded the cross-coupling product 1c in 60% yield accompanied with a byproduct 1b in 30% yield. Actually, we rechecked this reaction under the exact condition to find that the byproduct should be β-lactam 1a, which was identified unambiguously with full spectrographic and X-ray single-crystal analysis.
33. The CIF files of 1a, 5a, and 7a have been deposited with Cambridge Crystallographic Data Centre (nos. CCDC 945487, 945489, and 945488). These data can be obtained free of charge from CCDC via www.ccdc.cam.ac.uk/data-request/ cif.
34. Giri, R.; Maugel, N.; Foxman, B. M.; Yu, J.-Q. Organometallics 2008, 27, 1667.
35. MK-8712 was showed to have effective activity to inhibit class C β-lactamases both in vitro and vivo assays. (a) Heinze-Krauss, I.; Angehrn, P.; Charnas, R. L.; Gubernator, K.; Gutknecht, E.-M.; Hubschwerlen, C.; Kania, M.; Oefner, C.; Page, M. G. P.; Sogabe, S.; Specklin, J.-L.; Winkler, F. J. Med. Chem. 1998, 41, 3961
36. Blizzard, T. A.; Chen, H.; Kim, S.; Wu, J.; Young, K.; Park, Y. W.; Ogawa, A.; Raghoobar, S.; Painter, R. E.; Hairston, N.; Lee, S. H.; Misura, A.; Felcetto, T.; Fitzgerald, P.; Sharma, N.; Lu, J.; Ha, S.; Hickey, E.; Hermes, J.; Hammond, M. L. Bioorg. Med. Chem. Lett. 2010, 20, 918.
37. (c) Chen, H.; Blizzard, T. A.; Kim, S.; Wu, J.; Young, K.; Park, Y. W.; Ogawa, A. M.; Raghoobar, S.; Painter, R. E.; Wisniewski, D.; Hairston, N.; Fitzgerald, P.; Sharma, N.; Scapin, G.; Lu, J.; Hermes, J.; Hammond, M. Bioorg. Med. Chem. Lett. 2011, 21, 4267
38. Blizzard, T. A.; Chen, H. Y.; Wu, J. Y.; Kim, S.; Ha, S.; Mortko, C. J.; Variankaval, N.; Chiu, A. WO 2008039420 A2, 2008
39. Muller, M.; Wu, X.; Xu, L. WO 2009037229 A1, 2009.
40. The use of the removable MQ directing group was introduced by Chen and co-workers, see reference 11b.
41. (a) Klapars, A.; Parris, S.; Anderson, K. W.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 3529
42. Wasserman, H. H.; Matsuyama, H.; Robinson, R. P. Tetrahedron 2002, 58, 7177.