Visible-light-mediated α-arylation of enol acetates using aryl diazonium salts

Journal of Organic Chemistry

Volumn 77, Issue 22, 2012, Pages 10347-10352

  Hering, Thea ^a   Hari, Durga Prasad ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; ARYLDIAZONIUM SALTS; CONCISE SYNTHESIS; DIAZONIUM SALTS; RU(BPY); VISIBLE LIGHT;

AROMATIC COMPOUNDS; CHEMICAL REACTIONS;

SALTS;

ACETIC ACID DERIVATIVE; ALDEHYDE; DIAZONIUM COMPOUND; ENOL ACETATE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; ELECTRON TRANSPORT; IRRADIATION; LIGHT; PHOTOCATALYSIS; POLYMERIZATION; SYNTHESIS;

EID: 84869189955     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301984p     Document Type: Article

References (66)

1. Shen, T. V. Angew. Chem. 1972, 84, 512-526
2. Goehring, R. R.; Sachdeva, Y. P.; Pisipati, J. S.; Sleevi, M. C.; Wolfe, J. F. J. Am. Chem. Soc. 1985, 107, 435-443
3. Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147-2155
4. Kim, T. Y.; Kim, H. S.; Chung, Y. M.; Kim, J. N. Bull. Korean Chem. Soc. 2000, 21, 673-674
5. Olivera, R.; SanMartin, R.; Churruca, F.; Domínguez, E. J. Org. Chem. 2002, 67, 7215-7225
6. Ramajayam, R.; Giridhar, R.; Yadav, M. Chem. Heterocycl. Compd. 2006, 42, 901-906
7. Iwama, T.; Rawal, V. H. Org. Lett. 2006, 8, 5725-5728
8. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1983, 48, 2066-2069
9. Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168-15169
10. Sakakura, T.; Hara, M.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1985, 1545-1546
11. Molinaro, C.; Mowat, J.; Gosselin, F.; O'Shea, P. D.; Marcoux, J.-F.; Angelaud, R.; Davies, I. W. J. Org. Chem. 2007, 72, 1856-1858
12. Su, W.; Raders, S.; Verkade, J. G.; Liao, X.; Hartwig, J. F. Angew. Chem., Int. Ed. 2006, 45, 5852-5855
13. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676-707
14. Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109
15. Cao, C.; Wang, L.; Cai, Z.; Zhang, L.; Guo, J.; Pang, G.; Shi, Y. Eur. J. Org. Chem. 2011, 2011, 1570-1574
16. Liu, P.; Lanza, T. J., Jr.; Jewell, J. P.; Jones, C. P.; Hagmann, W. K.; Lin, L. S. Tetrahedron Lett. 2004, 44, 8869-8871
17. Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831-6833
18. Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5535-5538
19. Wu, X.-F.; Neumann, H.; Beller, M. Adv. Synth. Catal. 2011, 353, 788-792
20. Ge, S.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 16330-16333
21. Liu, C.; He, C.; Shi, W.; Chen, M.; Lei, A. Org. Lett. 2007, 9, 5601-5604
22. Liwosz, T. W.; Chemler, S. R. J. Am. Chem. Soc. 2012, 134, 2020-2023
23. He, C.; Guo, S.; Huang, L.; Lei, A. J. Am. Chem. Soc. 2010, 132, 8273-8275
24. Sävmarker, J.; Lindh, J.; Nilsson, P. Tetrahedron Lett. 2010, 51, 6886-6889
25. Song, C.-X.; Cai, G.-X.; Farrell, T. R.; Jiang, Z.-P.; Li, H.; Gan, L.-B.; Shi, Z.-J. Chem. Commun. 2009, 6002-6004
26. Minisci, F.; Coppa, F.; Fontana, F.; Pianese, G.; Zhao, L. J. Org. Chem. 1992, 57, 3929-3933
27. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
28. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527-532
29. Rueping, M.; Leonori, D.; Poisson, T. Chem. Commun. 2011, 47, 9615-9617
30. Teply, F. Collect. Czech. Chem. Commun. 2011, 76, 859-917
31. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828-6838
32. Busson, M.; Berisha, A.; Combellas, C.; Kanoufia, F.; Pinson, J. Chem. Commun. 2011, 47, 12631-12633
33. Galli, C. Chem. Rev. 1988, 88, 765-792
34. Kalyani, D.; McMurtrey, K. B.; Neufeldt, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18566-18569
35. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034-9037
36. Hari, D. P.; Schroll, P.; König, B. J. Am. Chem. Soc. 2012, 134, 2958-2961
37. Schroll, P.; Hari, D. P.; König, B. ChemistryOpen 2012, 1, 130-133
38. Sibi, M. P.; Renaud, P. Radicals in Organic Synthesis; Wiley-VCH Verlag GmbH: Weinheim, 2008; Vol. 2.
39. Allongue, P.; Delamar, M.; Desbat, B.; Fagebaume, O.; Hitmi, R.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1997, 119, 201-207
40. Heinrich, M. R. Chem.-Eur. J. 2009, 15, 820-833
41. Cano-Yelo, H.; Deronzier, A. J. Chem. Soc., Perkin Trans. 2 1984, 1093-1098
42. Cano-Yelo, H.; Deronzier, A. J. Photochem. 1987, 37, 315-321
43. Fidaly, K.; Ceballos, C.; Falguieres, A.; Veitia, M. S.-I.; Guy, A.; Ferroud, C. Green Chem. 2012, 14, 1293-1297
44. Neumann, M.; Földner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951-954
45. Mau, A. W. H.; Johansen, O.; Sasse, W. H. F. Photochem. Photobiol. 1985, 41, 503-509
46. Islam, S. D.-M.; Konishi, T.; Fujitsuka, M.; Ito, O.; Nakamura, Y.; Usui, Y. Photochem. Photobiol. 2000, 71, 675-680
47. Low yields observed for vinyl acetate 2i might also be due to photocatalytic radical polymerization: Yang, D. J. Photochem. Photobiol. 2008, 195, 323-329. Reference 7o reports yields of 60% in a similar reaction promoted by 2 equiv of Fe(II); under these conditions polymerization of 2i might be less favourable and the reaction could proceed via a different mechanism as Fe(II) can act not only as an electron donor, but also as a Lewis acid.
48. Fischer, E.; Hess, O. Ber. Dtsch. Chem. Ges 1884, 17, 559-568
49. Robinson, B. Chem. Rev. 1969, 69, 227-250
50. Vilsmeier, A.; Haack, A. Ber. Dtsch. Chem. Ges. 1927, 60, 119-122
51. Jutz, C. Chem. Ber. 1958, 91, 850-861
52. Hünig, S.; Kreitmeier, P.; Märkl, G.; Sauer, J. Arbeitsmethoden in der Organischen Chemie; Verlag Lehmanns: Munich, 2006.
53. Hanson, P.; Jones, J. R.; Taylor, A. B.; Walton, P. H.; Timms, A. W. J. Chem. Soc., Perkin Trans. 2 2002, 2, 1135-1150
54. Yasuda, M.; Chiba, K.; Ohigashi, N.; Katoh, Y.; Baba, A. J. Am. Chem. Soc. 2003, 125, 7291-7300
55. House, H. O.; Prabhu, A. V.; Phillips, W. V. J. Org. Chem. 1976, 41, 1209-1214
56. Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2011, 13, 2762-2765
57. Kosugi, M.; Miyajima, Y.; Nakanishi, H.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1989, 62, 3383-3385
58. Inaba, S.-I.; Rieke, R. D. J. Org. Chem. 1985, 50, 1373-1381
59. Li, L.; Cai, P.; Guo, Q.; Xue, S. J. Org. Chem. 2008, 73, 3516-3522
60. Gallardo, I.; Guirado, G.; Marquet, J. Eur. J. Org. Chem. 2002, 2002, 261-267
61. Shirude, S. T.; Patel, P.; Giridhar, R.; Yadav, M. R. Indian J. Chem. 2006, 45, 1080-1085
62. Grotjahn, D. B.; Lev, D. A. J. Am. Chem. Soc. 2004, 126, 12232-12233
63. Strazzolini, P.; Giumanini, A. G.; Runcio, A.; Scuccato, M. J. Org. Chem. 1998, 63, 952-958
64. Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996-4997
65. Kraus, G. A.; Guo, H. Org. Lett. 2008, 10, 3061-3063
66. Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Shirakawa, E.; Kawakami, Y. Angew. Chem., Int. Ed. 2005, 44, 1336-1340