Palladium-Catalyzed Formal Insertion of Carbenoids into Aminals via C-N Bond Activation

Journal of the American Chemical Society

Volumn 137, Issue 39, 2015, Pages 12490-12493

  Qin, Guiping ^a   Li, Lixin ^a   Li, Jiawen ^a   Huang, Hanmin ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CHEMICAL ACTIVATION; ORGANIC COMPOUNDS; ORGANOMETALLICS;

BOND ACTIVATION; CARBENOIDS; CATALYTIC CYCLES; DIAMINO ACIDS; MECHANISTIC STUDIES; METAL CARBENES; PALLADIUM-CATALYZED; QUARTER-NARY;

PALLADIUM;

AMINE; CARBENOID; CARBON; DIAMINO ACID; DIBENZYLAMINE; ESTER; FUNCTIONAL GROUP; NITROGEN; PALLADIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL BOND; ELECTROPHILICITY; NUCLEOPHILICITY; REACTION ANALYSIS; SYNTHESIS;

EID: 84943542743     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b08476     Document Type: Article

References (56)

1. Davies, H. M. L.; Beckwith, R. E. Chem. Rev. 2003, 103, 2861 10.1021/cr0200217
2. Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417 10.1038/nature06485
3. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704 10.1021/cr900239n
4. Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365 10.1021/ar300051u
5. Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 48, 10162 10.1039/c2cc34406h
6. Gillingham, D.; Fei, N. Chem. Soc. Rev. 2013, 42, 4918 10.1039/c3cs35496b
7. Wang, J. In Comprehensive Organic Chemistry III; Mingos, D. M. P.; Crabtree, R. H., Eds.; Elsevier: Oxford, 2007; pp 151-178.
8. Padwa, A.; Beall, L. S.; Eidell, C. K.; Worsencroft, K. J. J. Org. Chem. 2001, 66, 2414 10.1021/jo001684w
9. Clark, J. S.; Middleton, M. D. Org. Lett. 2002, 4, 765 10.1021/ol017240j
10. Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072 10.1021/jo049540v
11. Vanecko, J. A.; West, F. G. Org. Lett. 2005, 7, 2949 10.1021/ol050915o
12. Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011, 2011, 1015 10.1002/ejoc.201001588
13. Barluenga, J.; Valdés, C. Angew. Chem., Int. Ed. 2011, 50, 7486 10.1002/anie.201007961
14. Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560 10.1039/C1CS15127D
15. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236 10.1021/ar300101k
16. Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586 10.1021/cs4006666
17. Liu, Z.; Wang, J. J. Org. Chem. 2013, 78, 10024 10.1021/jo401850q
18. Peng, C.; Wang, Y.; Wang, J. J. Am. Chem. Soc. 2008, 130, 1566 10.1021/ja0782293
19. Kudirka, R.; Devine, S. K. J.; Adams, C. S.; VanVranken, D. L. Angew. Chem., Int. Ed. 2009, 48, 3677 10.1002/anie.200805483
20. Zhang, Z.; Liu, Y.; Gong, M.; Zhao, X.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2010, 49, 1139 10.1002/anie.200906349
21. Zhang, Z.; Liu, Y.; Ling, L.; Li, Y.; Dong, Y.; Gong, M.; Zhao, X.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 4330 10.1021/ja107351d
22. Zhou, L.; Ye, F.; Ma, J.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 3510 10.1002/anie.201007224
23. Chen, Z.-S.; Duan, X.-H.; Zhou, P.-X.; Ali, S.; Luo, J.-Y.; Liang, Y.-M. Angew. Chem., Int. Ed. 2012, 51, 1370 10.1002/anie.201106619
24. Ye, F.; Ma, X.; Xiao, Q.; Li, H.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2012, 134, 5742 10.1021/ja3004792
25. Hu, M.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2012, 134, 15257 10.1021/ja307058c
26. Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 775 10.1002/anie.201106825
27. Chan, W.-W.; Lo, S.-F.; Zhou, Z.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565 10.1021/ja305771y
28. Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670 10.1021/ja3062453
29. Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 5364 10.1021/ja402274g
30. Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 1364 10.1002/anie.201309650
31. Ye, F.; Qu, S.; Zhou, L.; Peng, C.; Wang, C.; Cheng, J.; Hossain, M. L.; Liu, Y.; Zhang, Y.; Wang, Z.-X.; Wang, J. J. Am. Chem. Soc. 2015, 137, 4435 10.1021/ja513275c
32. Murahashi, S.-l.; Imada, Y.; Nishimura, K. J. Chem. Soc., Chem. Commun. 1988, 1578 10.1039/c39880001578
33. Alper, H.; Urso, F.; Smith, D. J. H. J. Am. Chem. Soc. 1983, 105, 6737 10.1021/ja00360a045
34. Calet, S.; Urso, F.; Alper, H. J. Am. Chem. Soc. 1989, 111, 931 10.1021/ja00185a023
35. Roberto, D.; Alper, H. J. Am. Chem. Soc. 1989, 111, 7539 10.1021/ja00201a040
36. Wang, M.; Alper, H. J. Am. Chem. Soc. 1992, 114, 7018 10.1021/ja00044a010
37. Piotti, M. E.; Alper, H. J. Am. Chem. Soc. 1996, 118, 111 10.1021/ja9531586
38. Mahadevan, V.; Getzler, Y. D. Y. L.; Coates, G. W. Angew. Chem., Int. Ed. 2002, 41, 2781 10.1002/1521-3773(20020802)41:15<2781::AID-ANIE2781>3.0.CO;2-S
39. Liu, G.; Jia, L. Angew. Chem., Int. Ed. 2006, 45, 129 10.1002/anie.200502116
40. Hu, J.; Xie, Y.; Huang, H. Angew. Chem., Int. Ed. 2014, 53, 7272 10.1002/anie.201403774
41. Xie, Y.; Hu, J.; Wang, Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613 10.1021/ja310848x
42. Xie, Y.; Hu, J.; Xie, P.; Qian, B.; Huang, H. J. Am. Chem. Soc. 2013, 135, 18327 10.1021/ja410611b
43. Zhang, G.; Gao, B.; Huang, H. Angew. Chem., Int. Ed. 2015, 54, 7657 10.1002/anie.201502405
44. Albéniz, A. C.; Espinet, P.; Manrique, R.; Pérez-Mateo, A. Angew. Chem., Int. Ed. 2002, 41, 2363 10.1002/1521-3773(20020703)41:13<2363::AID-ANIE2363>3.0.CO;2-9
45. Bröring, M.; Brandt, C. D.; Stellwag, S. Chem. Commun. 2003, 2344 10.1039/b307160j
46. Fillion, E.; Taylor, N. J. J. Am. Chem. Soc. 2003, 125, 12700 10.1021/ja037409j
47. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardia, M.; Bonjoch, J. Organometallics 2004, 23, 1438 10.1021/om034270c
48. Albéniz, A. C.; Espinet, P.; Pérez-Mateo, A.; Nova, A.; Ujaque, G. Organometallics 2006, 25, 1293 10.1021/om051028s
49. Trépanier, V. é; Fillion, E. Organometallics 2007, 26, 30 10.1021/om0609416
50. Meana, I.; Albéniz, A. C.; Espinet, P. Organometallics 2012, 31, 5494 10.1021/om300462t
51. Viso, A.; Pradilla, R. F.; García, A.; Flores, A. Chem. Rev. 2005, 105, 3167 10.1021/cr0406561
52. CCDC 1405248 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data
53. Cheng, C.; Sun, J.; Xing, L.; Xu, J.; Wang, X.; Hu, Y. J. Org. Chem. 2009, 74, 5671 10.1021/jo9007282
54. Kobayashi, S.; Iimori, T.; Izawa, T.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 2406 10.1021/ja00399a044
55. Evans, C. S.; Qureshi, M. Y.; Bell, E. A. Phytochemistry 1977, 16, 565 10.1016/0031-9422(77)80016-2
56. Sammes, P. G. Chem. Rev. 1976, 76, 113 10.1021/cr60299a003