Reusable visible light photoredox catalysts; Catalyzed benzylic C(sp 3)-H functionalization/carbocyclization reactions

Synlett

Volumn 23, Issue 18, 2012, Pages 2707-2713

  Xia, Jia Dong ^a,b   Deng, Guo Bo ^a   Zhou, Ming Bo ^a   Liu, Wei ^a   Xie, Peng ^a,b   Li, Jin Heng ^a  

^a HUNAN UNIVERSITY   (China)

^b HUNAN NORMAL UNIVERSITY   (China)

Author keywords

alkynes; C H activation; catalysis; cyclization; indenes; photoredox

Indexed keywords

1 ISOPROPYL 2 (PHENYLETHYNYL)BENZENE; 4 NITROBENZENE 1 SULFONYL CHLORIDE; ALKYNE DERIVATIVE; BENZYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOCYCLIZATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ELECTRON TRANSPORT; PHOTOREDOX; STOICHIOMETRY; SYNTHESIS;

EID: 84867507370     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317349     Document Type: Article

References (75)

1. Zeitler K. Angew. Chem. Int. Ed.: 2009; 48 9785
2. Yoon T. P., Ischay M. A., Du J. Nature Chem.: 2010; 2 527
3. Narayanam J. M. R, Stephenson C. R. J. Chem. Soc. Rev.: 2011; 40 102
4. Tepl F. Collect. Czech. Chem. Commun.: 2011; 76 859
5. Tucker J. W., Stephenson C. R. J. J. Org. Chem.: 2012; 77 1617
6. Condie A. G., González-Gómez J., Stephenson C. R. J. J. Am. Chem. Soc.: 2010; 132 1464
7. Freeman D. B., Furst L., Condie A. G., Stephenson C. R. J. Org. Lett.: 2012; 14 94
8. Zou Y.-Q, Lu L.-Q, Fu L., Chang N.-J, Rong J., Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed.: 2011; 50 7171
9. Xuan J., Cheng Y., An J., Lu L.-Q, Zhang X.-X, Xiao W.-J. Chem. Commun.: 2011; 47 8337
10. Xie Z., Wang C., de Krafft K. E., Lin W. J. Am. Chem. Soc.: 2011; 133 2056
11. Zhu M., Zheng N. Synthesis: 2011; 2223
12. Rueping M., Leonori D., Poisson T. Chem. Commun.: 2011; 47 9615
13. Hari D. P., König B. Org. Lett.: 2011; 13 3852
14. Rueping M., Zhu S., Koenigs R. M. Chem. Commun.: 2011; 47 8679
15. Rueping M., Zoller J., Fabry D. C., Poscharny K., Koenigs R. M., Weirich T. E. Chem.-Eur. J.: 2012; 18 3478
16. Miyake Y., Nakajima K., Nishibayashi Y. J. Am. Chem. Soc.: 2012; 134 3338
17. For p -methoxybenzyl (PMB) ethers, see: Tucker J. W., Narayanam J. M. R, Shah P. S., Stephenson C. R. J. Chem. Commun.: 2011; 47 5040
18. For dialkylamides, see: Dai C., Meschini F., Narayanam J. M. R, Stephenson C. R. J. J. Org. Chem.: 2012; 77 4425
19. Pham P. V., Nagib D. A., MacMillan D. W. C. Angew. Chem. Int. Ed.: 2011; 50 6119
20. McNally A., Prier C. K., MacMillan D. W. C. Science: 2011; 334 1114
21. Nagib D. A., MacMillan D. W. C. Nature: 2011; 480 224
22. Lu Z., Shen M., Yoon T. P. J. Am. Chem. Soc.: 2011; 133 1162
23. Hurtley A. E., Cismesia M. A., Ischay M. A., Yoon T. P. Tetrahedron: 2011; 67 4442
24. Du J., Ruiz Espelt L., Guzei I. A., Yoon T. P. Chem. Sci.: 2011; 2 2115
25. Lin S., Ischay M. A., Fry C. G., Yoon T. P. J. Am. Chem. Soc.: 2011; 133 19350
26. Zou Y.-Q, Chen J.-R, Liu X.-P, Lu L.-Q, Davis R. L., Jorgensen K. A., Xiao W.-J. Angew. Chem. Int. Ed.: 2012; 51 784
27. Dai C., Narayanam J. M. R, Stephenson C. R. J. Nat. Chem.: 2011; 3 140
28. Nguyen J. D., Tucker J. W., Konieczynska M. D., Stephenson C. R. J. J. Am. Chem. Soc.: 2011; 133 3160
29. Kalyani D., McMurtrey K. B., Neufeldt S. R., Sanford M. S. J. Am. Chem. Soc.: 2011; 133 18566
30. Maity S., Zhu M., Shinabery R. S., Zheng N. Angew. Chem. Int. Ed.: 2012; 51 222
31. Giri R., Shi B.-F, Engle K. M., Maugel N., Yu J. Q. Chem. Soc. Rev.: 2009; 38 3242
32. Li C.-J. Acc. Chem. Res.: 2009; 42 335
33. Yoo W.-J, Li C.-J. Top. Curr. Chem.: 2010; 292 281
34. Wasa M., Engle K. M., Yu J.-Q. Isr. J. Chem.: 2010; 50 605
35. Yeung C. S., Dong V. M. Chem. Rev.: 2011; 111 1215
36. Newhouse T., Baran P. S. Angew. Chem. Int. Ed.: 2011; 50 3362
37. Zhang S.-Y, Zhang F.-M, Tu Y.-Q. Chem. Soc. Rev.: 2011; 40 1937
38. Tobisu M., Chatani N. Angew. Chem. Int. Ed.: 2006; 45 1683
39. Campos K. R. Chem. Soc. Rev.: 2007; 36 1069
40. Jazzar R., Hitce J., Renaudat A., Sofack-Kreutzer J., Baudoin O. Chem.-Eur. J.: 2010; 16 2654
41. Li H., Li B.-J, Shi Z.-J. Catal. Sci. Tech.: 2011; 1 191
42. Ramirez T. A., Zhao B., Shi Y. Chem. Soc. Rev.: 2012; 41 931
43. Bajracharya G. B., Pahadi N. K., Gridnev I. D., Yamatoto Y. J. Org. Chem.: 2006; 71 6204
44. Yang S., Li Z., Jian X., He C. Angew. Chem. Int. Ed.: 2009; 48 3999
45. Tobisu M., Nakai H., Chatani N. J. Org. Chem.: 2009; 74 5471
46. For Ru, see: Datta S., Odedra A., Liu R.-S. J. Am. Chem. Soc.: 2005; 127 11606
47. Odedra A., Datta S., Liu R.-S. J. Org. Chem.: 2007; 72 3289
48. For Rh, see: Shikanai D., Murase H., Hata T., Urabe H. J. Am. Chem. Soc.: 2009; 131 3166
49. For Pd, see: Zhao S.-C, Shu X.-Z, Ji K.-G, Zhou A.-X, He T., Liu X.-Y, Liang Y.-M. J. Org. Chem.: 2011; 76 1941
50. For Cu, see: Zeng X., Ilies L., Nakamura E. J. Am. Chem. Soc.: 2011; 133 17638
51. For Au, see: Bhunia S., Ghorpade S., Huple D. B., Liu R.-S. Angew. Chem. Int. Ed.: 2012; 51 2939
52. Morrison R. T., Boyd R. N. Organic Chemistry. 5th ed. Allyn and Bacon Boston: 1987
53. Dubbaka S. R., Vogel P. Angew. Chem. Int. Ed.: 2005; 44 7674
54. Kasahara A., Izumi T., Kudou N., Azami H., Yamamoto S. Chem. Ind. (London): 1988; 51
55. Miura M., Hashimoto H., Itoh K., Nomura M. Tetrahedron Lett.: 1989; 30 975
56. Dubbaka S. R., Vogel P. J. Am. Chem. Soc.: 2003; 125 15292
57. Dubbaka S. R., Vogel P. Tetrahedron Lett.: 2006; 47 3345
58. Volla C. M. R, Vogel P. Angew. Chem. Int. Ed.: 2008; 47 1305
59. Volla C. M. R, Dubbaka S. R., Vogel P. Tetrahedron: 2009; 65 504
60. Chen J., Sun Y., Liu B., Liu D., Cheng J. Chem. Commun.: 2012; 48 449
61. Lopes L. M. X, Yoshida M., Gottlieb O. R. Phytochemistry: 1984; 23 2021
62. Nagle D. G., Zhou Y.-D, Park P. U., Paul V. J., Rajbhandari I., Duncan C. J. G, Pasco D. S. J. Nat. Prod.: 2000; 63 1431
63. Sugimoto H., Iimura Y., Yamanishi Y., Yamatsu K. J. Med. Chem.: 1995; 38 4821
64. Dolling U.-H, Davis P., Grabowski E. J. J. J. Am. Chem. Soc.: 1984; 106 446
65. deSolms S. J., Woltersdorf O. W. Jr, Cragoe E. J. Jr, Watson L. S., Fanelli G. M. Jr. J. Med. Chem.: 1978; 21 437
66. Park C. H., Siomboing X., Yous S., Gressier B., Luyckx M., Chavatte P. Eur. J. Med. Chem.: 2002; 37 461
67. Anstead G. M., Wilson S. R., Katzenellenbogen J. A. J. Med. Chem.: 1989; 32 2163
68. Hajela K., Kapil R. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.: 1995; 34 361
69. Alcalde E., Mesquida N., López-Pérez S., Frigola J., Mercè R. J. Med. Chem.: 2009; 52 675
70. Ito T., Tanaka T., Iinuma M., Nakaya K., Takahashi Y., Sawa R., Murata J., Darnaedi D. J. Nat. Prod.: 2004; 67 932
71. Masamune S., Sakai M., Morio K. Can. J. Chem.: 1975; 53 784
72. Hanack M. Acc. Chem. Res.: 1976; 9 364
73. Dicoordinated Carbocations. Rappoport Z., Stang P. J. John Wiley & Sons Chichester: 1997
74. Okuyama T. Acc. Chem. Res.: 2002; 35 12
75. Okuyama T., Lodder G. In Advances in Physical Organic Chemistry. Tidwell T. T., Richard J. P. Elsevier Amsterdam: 2002; 1 56