Tandem [4 + 2]/[2 + 2] cycloaddition reactions involving indene or benzofurans and arynes

Organic Letters

Volumn 16, Issue 13, 2014, Pages 3576-3579

  Bhojgude, Sachin Suresh ^a   Thangaraj, Manikandan ^a   Suresh, Eringathodi ^b   Biju, Akkattu T ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84903740686     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501579d     Document Type: Article

References (42)

1. Wittig, G.; Pohmer, L. Chem. Ber. 1956, 89, 1334
2. Wittig, G.; Harborth, G. Ber. Dtsch. Chem. Ges. 1944, 77, 306
3. Wittig, G. Naturwissenschaften 1942, 30, 696
4. Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191
5. Wu, C.; Shi, F. Asian J. Org. Chem. 2013, 2, 116
6. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
7. Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766
8. Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140
9. Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520
10. Okuma, K. Heterocycles 2012, 85, 515
11. Yoshida, H.; Ohshita, J.; Kunai, A. Bull. Chem. Soc. Jpn. 2010, 83, 199
12. Chen, Y.; Larock, R. C. Arylation reactions involving the formation of arynes. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH Verlag: Weinheim, 2009; p 401.
13. Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215
14. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502
15. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
16. Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 483.
17. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
18. Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454
19. Thangaraj, M.; Bhojgude, S. S.; Bisht, R. H.; Gonnade, R. G.; Biju, A. T. J. Org. Chem. 2014, 79, 4757
20. Haneda, H.; Eda, S.; Aratani, M.; Hamura, T. Org. Lett. 2014, 16, 286
21. Kaicharla, T.; Bhojgude, S. S.; Biju, A. T. Org. Lett. 2012, 14, 6238
22. Li, J.; Wang, N.; Li, C.; Jia, X. Org. Lett. 2012, 14, 4994
23. Bhojgude, S. S.; Kaicharla, T.; Bhunia, A.; Biju, A. T. Org. Lett. 2012, 14, 4098
24. Buszek, K. R.; Luo, D.; Kondrashov, M.; Brown, N.; VanderVelde, D. Org. Lett. 2007, 9, 4135
25. Ikawa, T.; Takagi, A.; Kurita, Y.; Saito, K.; Azechi, K.; Egi, M.; Kakiguchi, K.; Kita, Y.; Akai, S. Angew. Chem., Int. Ed. 2010, 49, 5563
26. Dockendroff, C.; Sahil, S.; Olsen, M.; Milhau, L.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 15028
27. Criado, A.; Peña, D.; Cobas, A.; Guitián, E. Chem.-Eur. J. 2010, 16, 9736
28. Feltenberger, J. B.; Hayashi, R.; Tang, Y.; Babiash, E. S. C.; Hsung, R. P. Org. Lett. 2009, 11, 3666
29. Xie, C.; Zhang, Y. Org. Lett. 2007, 9, 781
30. Shou, W.-G.; Yang, Y.-Y.; Wang, Y.-G. J. Org. Chem. 2006, 71, 9241
31. Bhojgude, S. S.; Bhunia, A.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2014, 16, 676
32. Su, S.; Wang, N.; Li, C.; Song, B.; Jia, X.; Li, J. Asian J. Org. Chem. 2014, 3, 269
33. Siyang, H. X.; Wu, X. R.; Liu, H. L.; Wu, X. Y.; Liu, P. N. J. Org. Chem. 2014, 79, 1505
34. Hamura, T.; Arisawa, T.; Matsumoto, T.; Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 6842
35. Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Siegel, J. S.; Baldridge, K. K.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 10032
36. Hamura, T.; Ibusuki, Y.; Uekusa, H.; Matsumoto, T.; Suzuki, K. J. Am. Chem. Soc. 2006, 128, 3534
37. Hamura, T.; Hosoya, T.; Yamaguchi, H.; Kuriyama, Y.; Tanabe, M.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Helv. Chim. Acta 2002, 85, 3589
38. Anthony, I. J.; Wege, D. Aust. J. Chem. 1984, 37, 1283
39. CCDC-1005419 (3c) and CCDC-1005420 (6b) contain 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- request/cif.
40. Amin, S.; Balanikas, G.; Huie, K.; Hussain, N.; Geddie, J. E.; Hecht, S. S. J. Org. Chem. 1985, 50, 4642
41. Amin, S.; Hussain, N.; Brielmann, H.; Hecht, S. S. J. Org. Chem. 1984, 49, 1091
42. Amin, S.; Huie, K.; Hussain, N.; Balanikas, G.; Carmella, S. G.; Hecht, S. S. J. Org. Chem. 1986, 51, 1206