Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones

Organic Letters

Volumn 18, Issue 5, 2016, Pages 1048-1051

  Zhang, Zuxiao ^a   Tang, Xiao Jun ^a   Dolbier, William R ^a  

^a University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84960153972     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00168     Document Type: Article

References (64)

1. Kirsch, P. Modern Fluoroorganic Chemistry, 2 nd ed.; Wiley-VCH: Weinheim, 2013.
2. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881 10.1126/science.1131943
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320 10.1039/B610213C
4. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308 10.1039/B711844A
5. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, 2009.
6. Huchet, Q. A.; Kuhn, B.; Wagner, B.; Fischer, H.; Kansy, M.; Zimmerli, D.; Carreira, E. M.; Müller, K. J. Fluorine Chem. 2013, 152, 119 10.1016/j.jfluchem.2013.02.023
7. Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432 10.1021/cr4002879
8. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455 10.1021/cr100166a
9. Wu, X.-F.; Neumann, H.; Beller, M. Chem.-Asian J. 2012, 7, 1744 10.1002/asia.201200211
10. Macé, Y.; Magnier, E. Eur. J. Org. Chem. 2012, 2012, 2479 10.1002/ejoc.201101535
11. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214 10.1002/anie.201206566
12. Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617 10.1002/adsc.201200764
13. Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513 10.1021/ar4003202
14. Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2015, 115, 650 10.1021/cr500223h
15. Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683 10.1021/cr400473a
16. Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 48, 7465 10.1039/b916463d
17. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475 10.1021/cr1004293
18. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470 10.1038/nature10108
19. Wu, X.-F.; Neumann, H.; Beller, M. Chem.-Asian J. 2012, 7, 1744 10.1002/asia.201200211
20. Jin, Z.; Hammond, G. B.; Xu, B. Aldrichimica Acta 2012, 45, 67
21. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 2012, 6679 10.1002/ejoc.201200648
22. Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683 10.1021/cr400473a
23. Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626 10.1021/jo00111a021
24. Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560 10.1021/ol202289z
25. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 5524 10.1021/ja301013h
26. Prakash, G. K. S.; Ganesh, S. K.; Jones, J.-P.; Kulkarni, A.; Masood, K.; Swabeck, J. K.; Olah, G. A. Angew. Chem., Int. Ed. 2012, 51, 12090 10.1002/anie.201205850
27. Jiang, X.-L.; Chen, Z.-H.; Xu, X.-H.; Qing, F.-L. Org. Chem. Front. 2014, 1, 774 10.1039/C4QO00153B
28. Matheis, C.; Jouvin, K.; Goossen, L. Org. Lett. 2014, 16, 5984 10.1021/ol5030037
29. Gu, Y.; Leng, X.-B.; Shen, Q. Nat. Commun. 2014, 5, 5405 10.1038/ncomms6405
30. Fujiwara, Y.; Dixon, J. A.; Rodriguez, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494 10.1021/ja211422g
31. He, Z.; Tan, P.; Ni, C.; Hu, J. Org. Lett. 2015, 17, 1838 10.1021/acs.orglett.5b00308
32. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527 10.1038/nchem.687
33. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
34. Xuan, J.; Xiao, W. Angew. Chem., Int. Ed. 2012, 51, 6828 10.1002/anie.201200223
35. Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617 10.1021/jo202538x
36. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
37. Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387 10.1039/c3ob40137e
38. Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36 10.1016/j.tetlet.2013.10.090
39. Studer, A.; Curran, D. P. Angew. Chem., Int. Ed. 2016, 55, 58 10.1002/anie.201505090
40. Tang, X. J.; Thomoson, C. S.; Dolbier, W. R., Jr. Org. Lett. 2014, 16, 4594 10.1021/ol502163f
41. Tang, X. J.; Dolbier, W. R., Jr. Angew. Chem., Int. Ed. 2015, 54, 4246 10.1002/anie.201412199
42. Zhang, Z.; Tang, X. J.; Thomoson, C. S.; Dolbier, W. R., Jr. Org. Lett. 2015, 17, 3528 10.1021/acs.orglett.5b01616
43. Zhang, Z.; Tang, X. J.; Dolbier, W. R., Jr. Org. Lett. 2015, 17, 4401 10.1021/acs.orglett.5b02061
44. Tang, X. J.; Zhang, Z.; Dolbier, W. R., Jr. Chem.-Eur. J. 2015, 21, 18961 10.1002/chem.201504363
45. Wardrop, D. J.; Burge, M. S.; Zhang, W.; Ortiz, J. A. Tetrahedron Lett. 2003, 44, 2587 10.1016/S0040-4039(03)00227-2
46. Rishton, G. M.; Schwanz, M. A. Tetrahedron Lett. 1988, 29, 2643 10.1016/0040-4039(88)85248-1
47. Yang, Y. L.; Chang, F.-R.; Wu, Y.-C. Helv. Chim. Acta 2004, 87, 1392 10.1002/hlca.200490127
48. Kazmierski, W. M.; Furfine, E.; Spaltenstein, A.; Wright, L. L. Bioorg. Med. Chem. Lett. 2002, 12, 3431 10.1016/S0960-894X(02)00733-3
49. Albrightson, C. R.; Bugelski, P. J.; Berkhout, T. A.; Jackson, B.; Kerns, W. D.; Organ, A. J.; Badger, A. M. J. Pharmacol. Exp. Ther. 1995, 272, 689
50. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123 10.1021/cr940424+
51. Pape, A. P.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917 10.1021/cr9902852
52. Ortiz, F. L.; Iglesias, M. J.; Fernández, I.; Sánchez, C. M.; Gómez, G. R. Chem. Rev. 2007, 107, 1580 10.1021/cr030207l
53. Rousseaux, S.; García-Fortanet, J.; Sanchez, M. A. D. A.; Buchwald, S. L. J. Am. Chem. Soc. 2011, 133, 9282 10.1021/ja203644q
54. Mejorado, L. H.; Pettus, T. R. R. J. Am. Chem. Soc. 2006, 128, 15625 10.1021/ja062987w
55. Nicolaou, K. C.; Edmonds, D. J.; Li, A.; Tria, G. S. Angew. Chem., Int. Ed. 2007, 46, 3942 10.1002/anie.200700586
56. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068 10.1002/anie.201006017
57. Hey, D. H.; Todd, A. R. J. Chem. Soc. C 1967, 1518 10.1039/j39670001518
58. Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 5985 10.1016/S0040-4039(97)01362-2
59. Ibarra-Rivera, T. R.; Gámez-Montaño, R.; Miranda, L. D. Chem. Commun. 2007, 3485 10.1039/b705397e
60. Han, G.; Wang, Q.; Liu, Y.; Wang, Q. Org. Lett. 2014, 16, 5914 10.1021/ol502921a
61. Gao, F.; Yang, C.; Gao, G. L.; Zheng, L.; Xia, W. Org. Lett. 2015, 17, 3478 10.1021/acs.orglett.5b01530
62. Gu, Z.; Zhang, H.; Xu, P.; Cheng, Y.; Zhu, C. Adv. Synth. Catal. 2015, 357, 3057 10.1002/adsc.201500514
63. Han, G.; Liu, Y.; Wang, Q. Org. Lett. 2014, 16, 3188 10.1021/ol501054c
64. Han, G.; Wang, Q.; Liu, Y.; Wang, Q. Org. Lett. 2014, 16, 5914 10.1021/ol502921a