[3+2] cycloadditions of aryl cyclopropyl ketones by visible light photocatalysis

Journal of the American Chemical Society

Volumn 133, Issue 5, 2011, Pages 1162-1164

  Lu, Zhan ^a   Shen, Meihua ^a   Yoon, Tehshik P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITIONS; CYCLOPROPYL KETONES; ONE-ELECTRON REDUCTIONS; PHOTOCATALYTIC SYSTEMS; RADICAL ANIONS; RING SYSTEMS; RU(BPY); VISIBLE-LIGHT PHOTOCATALYSIS;

OLEFINS; ORGANIC COMPOUNDS; PHOTOCATALYSIS;

KETONES;

ALKENE; ANION; ARYL CYCLOPROPYL KETONE; CYCLOPENTANE; KETONE; LANTHANUM; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; CYCLOADDITION; IRRADIATION; LIGHT; PHOTOCATALYSIS;

ALKENES; CATALYSIS; FREE RADICALS; KETONES; LIGHT; PHOTOCHEMICAL PROCESSES;

EID: 79551693079     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107849y     Document Type: Article

References (56)

1. De Simone, F.; Waser, J. Synthesis 2009, 3353-3374 For a recent review, see
2. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364
3. Doyle, M. P. Chem. Rev. 1986, 86, 919-939
4. Lebel, H.; Marcoux, J. F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050
5. For recent reviews of donor-acceptor cyclopropane chemistry, see: Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
6. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321-347
7. Campbell, M. J.; Johnson, J. S.; Parsons, A. T.; Pohlhaus, P. D.; Sanders, S. D. J. Org. Chem. 2010, 75, 6317-3290
8. For recent reviews of methylene cyclopropane chemistry, see: Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77-151
9. Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589-635
10. Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213-1269
11. Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186-3189
12. Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312-6316
13. Carson, C. A; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051-3060
14. Jiao, L.; Ye, S.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 7178-7179
15. Jiao, L.; Lin, M.; Yu, Z.-X. Chem. Commun 2010, 46, 1059-1061
16. Li, Q.; Jiang, G.-J.; Jiao, L.; Yu, Z.-X. Org. Lett. 2010, 12, 1332-1335
17. Liu, L.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 5348-5349
18. Ogoshi, S.; Nagata, M.; Kurosawa, H. J. Am. Chem. Soc. 2006, 128, 5350-5351
19. Liu, L.; Montgomery, J. Org. Lett. 2007, 9, 3885-3887
20. Tamaki, T.; Nagata, M.; Ohashi, M.; Ogoshi, S. Chem.-Eur. J. 2009, 15, 10083-10091
21. Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886-12887
22. Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 14604-14605
23. For reviews on recent developments in transition metal photoredox catalysis in organic synthesis, see: Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785-9789
24. Narayanam, J. M. R. and Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
25. Yoon, T. P.; Ischay, M. A.; Du, J. Nature Chem. 2010, 2, 527-532
26. For recent reports synthetic applications of transition metal photoredox catalysis, see: Nicewicz, D.; MacMillan, D. W. C. Science 2008, 322, 77-80
27. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875-10877
28. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756-8757
29. Koike, T.; Akita, M. Chem. Lett. 2009, 38, 166-167
30. Tucker, J. W.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 368-371
31. Condie, A. G; González-Gómez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464-1465
32. Tucker, J. W.; Nguyen, J. D.; Narayanam, J. M. R.; Krabbe, S. W.; Stephenson, C. R. J. Chem. Commun. 2010, 46, 4985-4987
33. Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104-3107
34. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 7274-7276
35. Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600-13603
36. For seminal studies on the behavior of cyclopropyl ketyl radicals, see: Dauben, W. G.; Deviny, E. J. J. Org. Chem. 1966, 31, 3794-3798
37. Dauben, W. G.; Wolf, R. E. J. Org. Chem. 1970, 35, 2361-2367
38. Tanko, J. M.; Drumright, R. E. J. Am. Chem. Soc. 1990, 112, 5362-5363
39. Tanko, J. M.; Drumright, R. E. J. Am. Chem. Soc. 1992, 114, 1844-1854
40. Tanko, J. M.; Phillips, J. P. J. Am. Chem. Soc. 1999, 121, 6078-6079
41. Stevenson, J. P.; Jackson, W. F.; Tanko, J. M. J. Am. Chem. Soc. 2002, 124, 4271-4281
42. For early examples, see: Packer, R. A.; Whitehurst, J. S. J. Chem. Soc., Chem. Commun 1975, 757-758
43. White, J. D.; Torii, S.; Nogami, J. Tetrahedron Lett. 1974, 15, 2879-2882
44. Lafontaine, J.; Mongrain, M.; Sergent-Guay, M.; Ruest, L.; Deslongchamps, P. Can. J. Chem. 1980, 58, 2460-2476
45. White, J. D.; Ruppert, J. F.; Avery, M. A.; Torii, S.; Nokami, J. J. Am. Chem. Soc. 1981, 103, 1813-1821
46. For seminal examples of reductive cyclizations initiated by radical fragmentation of cyclopropyl ketones, see: Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211-6214
47. Cossy, J.; Furet, N.; BouzBouz, S. Tetrahedron 1995, 51, 11751-11764
48. Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885-8896
49. Enholm, E. J.; Jia, Z. J. Chem. Commun 1996, 1567-1568
50. Molander, G. A.; Alonso-Alija, C. Tetrahedron 1997, 53, 8067-8084
51. Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 174-181
52. Fagnoni, M.; Schmoldt, P.; Kirschberg, T.; Mattay, J. Tetrahedron 1998, 54, 6427-6444
53. Tzvetkov, N. T.; Neumann, B.; Stammler, H.-G.; Mattay, J. Eur. J. Org. Chem. 2006, 351-370
54. For a more complete discussion of the roles of the various reaction components, see refs 7a and 8c.
55. We were unable to isolate product, however, from the reactions of substrates with five-carbon tethers.
56. See Supporting Information for details.