Synthesis of Functionalized Dibenzothiophenes
[10] O. Takashi, F. Mayumi, S. Daiki, M. Keiji, Adv. Synth. Catal.
2001, 343, 166.
[11] C. P. Butts, L. Eberson, M. P. Hartshorn, F. Radner, W. T. Rob-
inson, B. R. Wood, Acta Chem. Scand. 1997, 51, 839.
[12] L. Benati, P. C. Montevecchi, A. Tundo, G. Zanardi, J. Chem.
Soc. Perkin Trans. 1 1974, 1272.
[13] K. Kawaguchi, K. Nakano, K. Nozaki, J. Org. Chem. 2007,
72, 5119.
[14] Z. Liu, R. C. Larock, Tetrahedron 2007, 63, 347.
[15] T. Dahl, C. W. Tornøe, B. Bang-Andersen, P. Nielsen, M.
Jørgensen, Angew. Chem. Int. Ed. 2008, 47, 1726; Angew.
Chem. 2008, 120, 1750.
[16] T. Migita, T. Shimizu, Y. Asami, J. Shiobara, Y. Kato, M. Ko-
sugi, Bull. Chem. Soc. Jpn. 1980, 53, 1385.
[17] M. A. Fernandez-Rodriguez, Q. Shen, J. F. Hartwig, J. Am.
Chem. Soc. 2006, 128, 2180.
[18] U. Schopfer, A. Schlapbach, Tetrahedron 2001, 57, 3069.
[19] M. Kosugi, T. Ogata, M. Terada, H. Sano, T. Migita, Bull.
Chem. Soc. Jpn. 1985, 58, 3657.
[20] M. Kreis, S. Bräse, Adv. Synth. Catal. 2005, 347, 313.
[21] T. Itoh, T. Mase, Org. Lett. 2004, 6, 4587.
[22] N. Miyaura in Metal-Catalyzed Cross-Coupling Reactions, 2nd
ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim,
2004.
[23] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
[24] The relatively low reactivity of the thiophenol facilitates a pos-
sibility for selectivity of a subsequent Pd-catalyzed cyclization
by employing a bromide as a competing alternative to the SNAr
cyclization.
[25] CCDC-792961, -792962, -792963, -792964, -792965, -792966,
-792967 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.
Supporting Information (see footnote on the first page of this arti-
cle): Experimental procedures and characterization data along with
copies of NMR spectra.
[1]
[2]
T. C. Ho, Catal. Today 2004, 98, 3.
S. Martin-Santamaria, J.-J. Rodriguez, S. de Pascual-Teresa, S.
Gordon, M. Bengtsson, I. Garrido-Laguna, B. Rubio-Viqueira,
P. P. Lopez-Casas, M. Hidalgo, B. de Pascual-Teresa, A.
Ramos, Org. Biomol. Chem. 2008, 6, 3486.
[3]
a) J. Gao, L. Li, Q. Meng, R. Li, H. Jiang, H. Li, W. Hu,
J. Mater. Chem. 2007, 17, 1421; b) Y. Wang, S. R. Parkin, J.
Gierschner, M. D. Watson, Org. Lett. 2008, 10, 3307; c) V. K.
Olkhovik, D. A. Vasilevskii, A. A. Pap, G. V. Kalechyts, Y. V.
Matveienko, A. G. Baran, N. A. Halinouski, V. G. Petushok,
Arkivoc 2008, 9, 69; d) F. B. Dias, K. T. Kamtekar, T. Cazati,
G. Williams, M. R. Bryce, A. P. Monkman, ChemPhysChem
2009, 10, 2096; e) H. Li, A. S. Batsanov, K. C. Moss, H. L.
Vaughan, F. B. Dias, K. T. Kamtekar, M. R. Bryce, A. P.
Monkman, Chem. Commun. 2010, 4812; f) P. K. Nayak, N.
Agarwal, N. Periasamy, J. Chem. Sci. 2010, 122, 119.
[4]
a) T. Ganguly, L. Farmer, W. Li, J. Y. Bergeron, D. Gravel, G.
Durocher, Macromolecules 1993, 26, 2315; b) T. Ganguly, W.
Li, J. Y. Bergeron, L. Farmer, D. Gravel, G. Durocher, J. Lu-
min. 1994, 59, 247; c) J. Bouchard, S. Wakim, M. Leclerc, J.
Org. Chem. 2004, 69, 5705; d) M. Biswas, S. K. Das, Eur. Po-
lym. J. 1981, 17, 1245; e) M. Bisvvas, S. K. Das, Polymer 1982,
23, 1713; f) T. Kokubun, J. B. Harborne, J. Eagles, P. G. Water-
man, Phytochemistry 1995, 39, 1039.
[5] a) C. Courtot, L. Nicolas, T. H. Liang, C. R. Hebd. Seances
Acad. Sci. 1928, 186, 1624; b) J. Korang, W. R. Grither, R. D.
McCulla, J. Am. Chem. Soc. 2010, 132, 4466.
[6] N. M. Cullinane, C. G. Davies, G. I. Davies, J. Chem. Soc.
1936, 1435.
[7] H. Gilman, A. L. Jacoby, J. Org. Chem. 1938, 3, 108.
[8] N. Arnau, M. Moreno-Manas, R. Pleixats, Tetrahedron 1993,
49, 11019.
[26] R. M. Schaffrin, J. Trotter, J. Chem. Soc. A 1970, 1561.
[27] D. Yamazaki, T. Nishinaga, K. Komatsu, Org. Lett. 2004, 6,
4179.
[28] L. V. Dunkerton, A. Pandey, P. D. Robinson, Acta Crystallogr.,
Sect. C 1989, 45, 343.
[9] R. Sanz, Y. Fernandez, M. P. Castroviejo, A. Perez, F. J.
Fañanás, J. Org. Chem. 2006, 71, 6291.
[29] J. D. Dunitz, ChemBioChem 2004, 5, 614.
Received: October 11, 2010
Published Online: November 17, 2010
Eur. J. Org. Chem. 2011, 53–57
© 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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