Organic Letters
Letter
(4) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.;
Murai, S. J. Am. Chem. Soc. 2001, 123, 10935.
(5) (a) Jun, C.-H. Chem. Commun. 1998, 1405. (b) Dastbaravardeh,
Scheme 2. Methods for Removal of the Benzoxazol-2-yl
Group
N.; Kirchner, K.; Schnurch, M.; Mihovilovic, M. D. J. Org. Chem. 2012,
̈
78, 658. (c) Dastbaravardeh, N.; Schnurch, M.; Mihovilovic, M. D. Eur.
̈
́
J. Org. Chem. 2013, 2878. (d) Prokopcova, H.; Bergman, S. D.;
Aelvoet, K.; Smout, V.; Herrebout, W.; Van der Veken, B.; Meerpoel,
L.; Maes, B. U. W. Chem.Eur. J. 2010, 16, 13063.
(6) (a) Smout, V.; Peschiulli, A.; Verbeeck, S.; Mitchell, E. A.;
Herrebout, W.; Bultinck, P.; Vande Velde, C. M. L.; Berthelot, D.;
Meerpoel, L.; Maes, B. U. W. J. Org. Chem. 2013, 78, 9803. (b) Jana,
C. K.; Grimme, S.; Studer, A. Chem.Eur. J. 2009, 15, 9078.
(7) Rondestvedt, C. S.; Davis, S. J. J. Org. Chem. 1957, 22, 200.
(8) (a) Green, M.; Kuc, T. A.; Taylor, S. H. J. Chem. Soc. A 1971,
2334. (b) Wang, C.; Chen, H.; Wang, Z.; Chen, J.; Huang, Y. Angew.
Chem. 2012, 124, 7354.
(9) (a) Pan, S.; Shibata, T. ACS Catal. 2013, 3, 704. (b) Su, Y.; Song,
G.; Han, K.; Li, X. J. Organomet. Chem. 2011, 696, 1640.
(10) (a) Tsuchikama, K.; Kasagawa, M.; Hashimoto, Y.-K.; Endo, K.;
Shibata, T. J. Organomet. Chem. 2008, 693, 3939. (b) Pan, S.; Ryu, N.;
Shibata, T. Adv. Synth. Catal. 2014, 356, 929.
(11) For Pd-catalyzed ortho-functionalizations of 2-arylbenzoxazoles,
see: (a) Yang, F.; Wu, Y.; Zhu, Z.; Zhang, J.; Li, Y. Tetrahedron. 2008,
64, 6782. (b) Banerjee, A.; Santra, S. K.; Guin, S.; Rout, S. K.; Patel, B.
K. Eur. J. Org. Chem. 2013, 2013, 1367.
(12) (a) Froehr, T.; Sindlinger, C. P.; Kloeckner, U.; Finkbeiner, P.;
Nachtsheim, B. J. Org. Lett. 2011, 13, 3754. (b) Kloeckner, U.;
Weckenmann, N. M.; Nachtsheim, B. J. Synlett 2012, 2012, 97.
(13) Gim, H. J.; Cheon, Y.-J.; Ryu, J.-H.; Jeon, R. Bioorg. Med. Chem.
Lett. 2011, 21, 3057.
imposed by the peri-hydrogen in position 8 in the intermediate
Ir hydrido complex may account for the observed behavior
although DFT calculations are not conclusive to date.
ASSOCIATED CONTENT
■
S
* Supporting Information
Experimental procedures, characterization data, H, 13C, and
1
2D NMR spectra. This material is available free of charge via
(14) (a) Schinkel, M.; Wang, L.; Bielefeld, K.; Ackermann, L. Org.
Lett. 2014, 16, 1876. (b) Ogiwara, Y.; Tamura, M.; Kochi, T.;
Matsuura, Y.; Chatani, N.; Kakiuchi, F. Organometallics 2013, 33, 402.
(c) Pan, S.; Ryu, N.; Shibata, T. J. Am. Chem. Soc. 2012, 134, 17474.
(15) (a) Rueping, M.; Vila, C.; Koenigs, R. M.; Poscharny, K.; Fabry,
D. C. Chem. Commun. 2011, 47, 2360. (b) Kohls, P.; Jadhav, D.;
Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672. (c) Ruiz Espelt, L.;
Wiensch, E. M.; Yoon, T. P. J. Org. Chem. 2013, 78, 4107.
(d) Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J.
Org. Lett. 2012, 14, 94.
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We thank Dr. J. C. Liermann (Mainz) for NMR spectroscopy
and Dr. N. Hanold (Mainz) for mass spectrometry. The expert
technical assistance of D. Kowalczyk (Mainz) is gratefully
acknowledged.
̀
(16) (a) Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Fares, C.;
Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106. (b) Shen, Y.; Li, M.;
Wang, S.; Zhan, T.; Tan, Z.; Guo, C.-C. Chem. Commun. 2009, 953.
(17) Ghobrial, M.; Harhammer, K.; Mihovilovic, M. D.; Schnurch, M.
̈
Chem. Commun. 2010, 46, 8836.
(18) Louafi, F.; Moreau, J.; Shahane, S.; Golhen, S.; Roisnel, T.;
Sinbandhit, S.; Hurvois, J.-P. J. Org. Chem. 2011, 76, 9720.
(19) Takebayashi, S.; Shibata, T. Organometallics 2012, 31, 4114.
(20) Shibata, T.; Shizuno, T. Angew. Chem., Int. Ed. 2014, 53, 5410.
(21) (a) Pan, S.; Endo, K.; Shibata, T. Org. Lett. 2011, 13, 4692.
(b) Pan, S.; Matsuo, Y.; Endo, K.; Shibata, T. Tetrahedron 2012, 68,
9009.
(22) Yotphan, S.; Beukeaw, D.; Reutrakul, V. Synthesis 2013, 45, 936.
(23) Mitchell, E. A.; Peschiulli, A.; Lefevre, N.; Meerpoel, L.; Maes,
B. U. W. Chem.Eur. J. 2012, 18, 10092.
REFERENCES
■
(1) (a) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F.
Angew. Chem., Int. Ed. 2012, 51, 10236. (b) Satoh, T.; Miura, M.
Chem.Eur. J. 2010, 16, 11212. (c) Andreatta, J. R.; McKeown, B. A.;
Gunnoe, T. B. J. Organomet. Chem. 2011, 696, 305. (d) Nakao, Y.
Chem. Rec. 2011, 11, 242. (e) Foley, N. A.; Lee, J. P.; Ke, Z.; Gunnoe,
T. B.; Cundari, T. R. Acc. Chem. Res. 2009, 42, 585. (f) Godula, K.;
Sames, D. Science 2006, 312, 67. (g) Jazzar, R.; Hitce, J.; Renaudat, A.;
Sofack-Kreutzer, J.; Baudoin, O. Chem.Eur. J. 2010, 16, 2654.
(2) (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.;
Sonoda, M.; Chatani, N. Nature 1993, 366, 529. (b) Rakshit, S.;
Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133,
2350. For selected reviews on chelation-assisted C−H activation, see:
(c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
(d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem.Eur. J. 2002, 8, 2422.
(e) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed.
2009, 48, 9792. (f) Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J.
A. Acc. Chem. Res. 2011, 45, 814. (g) Rouquet, G.; Chatani, N. Angew.
Chem., Int. Ed. 2013, 52, 11726. (h) Zhang, F.; Spring, D. R. Chem.
Soc. Rev. 2014, DOI: 10.1039/c4cs00137k.
(3) (a) Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450.
(b) Fan, M.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 12152.
(c) Rodriguez, N.; Romero-Revilla, J. A.; Fernandez-Ibanez, M. A.;
Carretero, J. C. Chem. Sci. 2013, 4, 175.
C
dx.doi.org/10.1021/ol501935d | Org. Lett. XXXX, XXX, XXX−XXX