Highly selective insertion of arynes into a C(sp)-O(sp3) σ Bond

Organic Letters

Volumn 13, Issue 5, 2011, Pages 960-963

  Ła̧czkowski, Krzysztof Z ^a,b   García, Diego ^a   Peña, Diego ^a   Cobas, Agustín ^a   Pérez, Dolores ^a   Guitián, Enrique ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952181718     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol103001k     Document Type: Article

References (36)

1. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
2. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
3. Peña, D.; Pérez, D.; Guitián, E. Heterocycles 2007, 74, 89
4. Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215
5. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
6. For example, benzyne precursor 1a is a commercially available compound which can be easily obtained in high yield from o -bromophenol by a one-pot procedure. See: Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454
7. Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., Int. Ed. 1998, 37, 2659
8. Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827
9. Guitián, E.; Pérez, D.; Peña, D. In Topics in Organometallic Chemistry; Tsuji, J., Ed.; Springer-Verlag: Weinheim, 2005; Vol. 14, pp 109 -146.
10. For some recent examples, see: Bhuvaneswary, S.; Jeganmohan, M.; Cheng, C.-H. Chem. Commun. 2008, 5013
11. Xie, C.; Liu, L.; Zhang, Y.; Xu, P. Org. Lett. 2008, 10, 2393
12. Jeganmohan, M.; Bhuvaneswari, S.; Cheng, C.-H. Angew. Chem., Int. Ed. 2008, 47, 1
13. Hsieh, J.-C.; Cheng, C.-H. Chem. Commun. 2008, 2992
14. Xie, C.; Zhang, Y.; Yang, Y. Chem. Commun. 2008, 4810
15. Worlikar, S. A.; Larock, R. C. Org. Lett. 2009, 11, 2413
16. Qiu, Z.; Xie, Z. Angew. Chem., Int. Ed. 2009, 48, 5729
17. Yoshida, H.; Morishita, T.; Nakata, H.; Ohshita, J. Org. Lett. 2009, 11, 373
18. Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579
19. Yoshida, H.; Okada, K.; Kawashima, S.; Tanino, K.; Ohshita, J. Chem. Commun. 2010, 46, 1763
20. Toledo, F. T.; Marques, H.; Comasseto, J. V.; Raminelli, C. Tetrahedron Lett. 2007, 48, 8125
21. Liu, Y. -L.; Liang, Y.; Pi, S. -F.; Li, J. -H. J. Org. Chem. 2009, 74, 5691
22. Krishnan, S.; Bagdanoff, J. T.; Ebner, D. C.; Ramtohul, Y. K.; Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 13745
23. Huang, X.; Xue, J. J. Org. Chem. 2007, 72, 3965
24. Yoshida, H.; Kishida, T.; Watanabe, M.; Ohshita, J. Chem. Commun. 2008, 5963
25. Yoshida, H.; Morishita, T.; Ohshita, J. Chem. Lett. 2010, 39, 508
26. Pintori, D. G.; Greaney, M. F. Org. Lett. 2010, 12, 168
27. Yoshioka, E.; Kohtani, S.; Miyabe, H. Org. Lett. 2010, 12, 1956
28. Yoshida, H.; Mimura, Y.; Ohshita, J.; Kunai, A. Chem. Commun. 2007, 2405
29. Morishita, T.; Yoshida, H.; Ohshita, J. Chem. Commun. 2010, 640
30. Beltrán-Rodil, S.; Peña, D.; Guitián, E. Synlett 2007, 1308
31. Stiles, M.; Burkhardt, U.; Haag, A. J. Org. Chem. 1962, 27, 4715
32. Arylacetylenes are very useful moieties for various synthetic procedures such as azide-alkyne Huisgen cycloaddition, Sonogashira coupling, or poly(aryl acetylene) synthesis.
33. Ishizaki, M.; Ozaki, K.; Kanematsu, A.; Isoda, T.; Hoshino, O. J. Org. Chem. 1993, 58, 3877
34. XPhos: 2-dicyclohexylphosphino-2′,4′,6′- triisopropylbiphenyl. See: Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653
35. The structures of both regioisomers were confirmed by comparison with a sample of 3e′ obtained by an independent synthesis.
36. See the Supporting Information for details.