Direct access to fluorene by successive C-O/C-H bond activations of 2-phenylbenzyl ester

Organometallics

Volumn 33, Issue 8, 2014, Pages 1921-1924

  Hirano, Masafumi ^a   Kawazu, Sosuke ^a   Komine, Nobuyuki ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; PALLADIUM COMPOUNDS;

BOND ACTIVATION; C-H BOND CLEAVAGE; CARBOXYLATO; CATALYTIC FORMATION; ELECTROPHILIC SUBSTITUTIONS; FLUORENES; OXIDATIVE ADDITIONS; TRIFLUOROACETATES;

ESTERS;

EID: 84899576167     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om5001869     Document Type: Article

References (34)

1. Ackermann, L. Chem. Rev. 2011, 111, 1315
2. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
3. Oxgaard, J.; Tenn, W. J., III; Nielsen, R. J.; Periana, R. A.; Goddard, W. A., III Organometallics 2007, 26, 1565
4. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 29, 1118
5. Winstein, S.; Traylor, T. G. J. Am. Chem. Soc. 1955, 77, 3747
6. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5820
7. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5887
8. Komiya, S.; Hirano, M. In Fundamentals of Molecular Catalysis; Kurosawa, H.; Yamamoto, A., Eds.; Elsevier: Amsterdam, 2003; p 115.
9. Ling, Y.-S.; Yamamoto, A. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, 1999; p 161.
10. Yamamoto, A. Adv. Organomet. Chem. 1992, 34, 111
11. Vinyl ester by Pt(0): Manbeck, K. A.; Kundu, S.; Walsh, A. P.; Brennessel, W. W.; Jones, W. D. Organometallics 2012, 31, 5018
12. Recent direct C-H arylation using alkenyl acetate: Ogiwara, Y.; Tamura, M.; Kochi, T.; Matsuura, Y.; Chatani, N.; Kakiuchi, F. Organometallics 2014, 33, 402
13. Muto, K.; Yamaguchi, J.; Lei, A.; Itami, K. J. Am. Chem. Soc. 2013, 135, 16384
14. Guan, B.-T.; Wang, Y.; Li, B.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468
15. Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422
16. Kuwano, R.; Kondo, Y. Org. Lett. 2004, 6, 3545
17. Recent C-O/C-H activations of benzyl phosphates: Ackermann, L.; Barfüsser, S.; Pospech, J. Org. Lett. 2010, 12, 724
18. Komiya, S.; Kabasawa, T.; Yamashita, K.; Hirano, M.; Fukuoka, A. J. Organomet. Chem. 1994, 471, C6
19. Planas, J. G.; Marumo, T.; Ichikawa, Y.; Hirano, M.; Komiya, S. J. Mol. Catal. A 1999, 147, 137
20. Hirano, M.; Fujimoto, R.; Hatagami, K.; Komine, N.; Komiya, S. ChemCatChem 2013, 5, 1101
21. Li, Y. Acc. Chem. Res. 2012, 45, 723
22. Zotti, G.; Berlin, B. V. Acc. Chem. Res. 2008, 41, 1098
23. Hwang, S. J.; Kim, H. J.; Chang, S. Org. Lett. 2009, 11, 4588
24. Nagayama, K.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1999, 72, 799
25. w) = 0.0738 (0.2091). CCDC No. 986963 contains supplementary crystallographic data for 2. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/data-request/cif.
26. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5 th ed.; Wiley: New York, 1997; Part B, p 59.
27. Mandai, T.; Matsumoto, T.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1993, 34, 2531
28. Kozhushkov, S. I.; Potukuchi, H. K.; Ackermann, L. Catal. Sci. Technol. 2013, 3, 526
29. Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 2000, 19, 3895
30. Davies, L. D.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754
31. Gorelsky, S. I. Organometallics 2012, 31, 4631
32. Tan, Y.; Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 3683
33. Wakioka, M.; Nakamura, Y.; Wang, Q.; Ozawa, F. Organometallics 2012, 31, 4810
34. Raybov, A. D. Chem. Rev. 1990, 90, 403