Regioselective insertion of carborynes into ethereal C-H bond: Facile synthesis of α-carboranylated ethers

Journal of the American Chemical Society

Volumn 133, Issue 15, 2011, Pages 5760-5763

  Wang, Sunewang R ^a   Qiu, Zaozao ^a   Xie, Zuowei ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ETHERS; C-H BOND; CARBORANES; FACILE SYNTHESIS; FUNCTIONALIZED; REGIO-SELECTIVE; ROOM TEMPERATURE; UV IRRADIATION;

ETHERS; ORGANIC COMPOUNDS;

REGIOSELECTIVITY;

ALKYL ETHER; CARBON; CARBORANE DERIVATIVE; ETHER DERIVATIVE; HYDROGEN;

ARTICLE; CHEMICAL BOND; ELIMINATION REACTION; ROOM TEMPERATURE; ULTRAVIOLET RADIATION;

EID: 79954500075     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201126h     Document Type: Article

References (39)

1. Fokin, A. A.; Schreiner, P. R. Chem. Rev. 2002, 102, 1551-1593
2. Ortiz de Montellano, P. R. Chem. Rev. 2010, 110, 932-948
3. Selected examples of radical C-H bond functionalization, see: Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Am. Chem. Soc. 2005, 127, 11610-11611
4. Akindele, T.; Yamada, K.; Tomioka, K. Acc. Chem. Res. 2009, 42, 345-355
5. Liu, L.; Floreancig, P. E. Angew. Chem., Int. Ed. 2010, 49, 3069-3072
6. Yoshikai, N.; Mieczkowski, A.; Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 5568-5569
7. Pan, S.; Liu, J.; Li, H.; Wang, Z.; Guo, X.; Li, Z. Org. Lett. 2010, 12, 1932-1935
8. Tzirakis, M. D.; Orfanopoulos, M. Angew. Chem., Int. Ed. 2010, 49, 5891-5893
9. Godula, K.; Sames, D. Science 2006, 312, 67-72
10. Bergman, R. G. Nature 2007, 446, 391-393
11. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
12. Shul'pin, G. B. Org. Biomol. Chem. 2010, 8, 4217-4228
13. 3 C-H bonds, see: Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069-1084
14. Li, C.-J. Acc. Chem. Res. 2009, 42, 335-344
15. Doyle, M. P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704-724
16. Conejero, S.; Paneque, M.; Poveda, M. L.; Santos, L. L.; Carmona, E. Acc. Chem. Res. 2010, 43, 572-580
17. Gingrich, H. L.; Ghosh, T.; Huang, Q.; Jones, M., Jr. J. Am. Chem. Soc. 1990, 112, 4082-4083
18. Ghosh, T.; Gingrich, H. L.; Kam, C. K.; Mobraaten, E. C.; Jones, M., Jr. J. Am. Chem. Soc. 1991, 113, 1313-1318
19. Gingrich, H. L.; Huang, Q.; Morales, A. L.; Jones, M., Jr. J. Org. Chem. 1992, 57, 3803-3806
20. Gingrich, H. L.; Ghosh, T.; Huang, Q.; Li, J.; Jones, M., Jr. Pure Appl. Chem. 1993, 65, 65-71
21. Ho, D. M.; Cunningham, R. J.; Brewer, J. A.; Bian, N.; Jones, M., Jr. Inorg. Chem. 1995, 34, 5274-5278
22. Atkins, J. H.; Ho, D. M.; Jones, M., Jr. Tetrahedron Lett. 1996, 37, 7217-7220
23. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic: New York, 1967.
24. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701-730
25. Jeon, J.; Kitamura, T.; Yoo, B.-W.; Kang, S. O.; Ko, J. Chem. Commun. 2001, 2110-2111
26. Lee, T.; Jeon, J.; Song, K. H.; Jung, I.; Baik, C.; Park, K.-M.; Lee, S. S.; Kang, S. O.; Ko, J. Dalton Trans. 2004, 933-937
27. Qiu, Z.; Wang, S. R.; Xie, Z. Angew. Chem., Int. Ed. 2010, 49, 4649-4652 For metal-carboryne chemistry developed in our lab, see: Deng, L.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2006, 128, 7728-7729
28. Qiu, Z.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 2084-2085
29. Ren, S.; Chan, H.-S.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 3862-3863
30. Qiu, Z.; Xie, Z. J. Am. Chem. Soc. 2010, 132, 16085-16093
31. Wang, S. R.; Qiu, Z.; Xie, Z. J. Am. Chem. Soc. 2010, 132, 9988-9989
32. Beltrán-Rodil, S.; Peña, D.; Guitián, E. Synlett 2007, 1308-1310
33. Okuma, K.; Fukuzaki, Y.; Nojima, A.; Shioji, K.; Yokomori, Y. Tetrahedron. Lett. 2008, 49, 3063-3066
34. Feltenberger, J. B.; Hayashi, R.; Tang, Y.; Babash, E. S. C.; Hsung, R. P. Org. Lett. 2009, 11, 3666-3669 For a review on insertion of benzyne into other σ bonds, see: Peañ, D.; Prez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579-3581
35. For experimental details, complete characterization data, and X-ray data, see the Supporting Information.
36. It was reported that UV exposure from sitting under fluorescent lights for 8 h is equivalent to 1 min of midday solar exposure on a clear July day in Washington, D.C. Lytle, C.; Cyr, W.; Beer, J.; Miller, S.; James, R.; Landry, R.; Jacobs, M.; Kaczmarek, R.; Sharkness, C.; Gaylor, D.; Gruijl, F.; Van Der Leun, J. Photodermatol. Photoimmunol. Photomed. 1993, 9, 268-274
37. 2) at 15 cm: 300 (365 nm) and 310 (254 nm).
38. Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2005, 70, 2342-2345
39. Puga, A. V.; Teixidor, F.; Sillanpää, R.; Kivekäs, R.; Arca, M.; Barberà, G.; Viñas, C. Chem.-Eur. J. 2009, 15, 9755-9763