LETTER
Pd-Catalyzed Coupling Reaction of Diaryl Dichalcogenide with Aryl Bromide
2147
(5) For examples of the palladium-catalyzed coupling reaction,
see: (a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett.
1978, 13. (b) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara,
J.-i.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53,
1385. (c) Zheng, N.; McWilliams, J. C.; Fleitz, F. J.;
Armstrong, J. D. III; Volante, R. P. J. Org. Chem. 1998, 63,
9606. (d) Schopfer, U.; Schlapbach, A. Tetrahedron 2001,
57, 3069. (e) Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org.
Chem. 2001, 66, 8677. (f) Li, G. Y. Angew. Chem. Int. Ed.
2001, 40, 1513. (g) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
(h) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
(11) Typical experimental procedure: Diphenyl disulfide (109
mg, 0.5 mmol), PdCl2(dppf) (37 mg, 0.05 mmol), and zinc
(80 mg, 1.2 mmol), were placed in a round-bottom flask
containing a stirring bar, and a THF solution (5 mL) of the
aryl bromide (1.0 mmol) was then added to the flask, and the
resulting mixture was heated at reflux for 24 h. After cooling
to r.t., the mixture was diluted with Et2O (30 mL). The
precipitate was removed by filtration and the filtrate was
washed with brine and dried (Na2SO4). A GC-MS analysis
of the ethereal solution showed the presence of the
corresponding unsymmetrical sulfide, and the yield was
determined using biphenyl as an internal standard. The aryl
sulfide was isolated by PTLC and fully characterized.
(12) The reaction with p-iodonitrobenzene proceeded to give the
corresponding aryl sulfide in 82% yield.
(i) Fernãndez-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J.
Am. Chem. Soc. 2006, 128, 2180.
(6) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000,
2, 2019.
(7) (a) Taniguchi, N. J. Org. Chem. 2004, 69, 6904.
(b) Taniguchi, N.; Onami, T. Synlett 2003, 829.
(c) Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
(d) Millois, C.; Diaz, P. Org. Lett. 2000, 2, 1705.
(8) For examples, see: (a) Organoselenium Chemistry: A
Practical Approach in Chemistry; Back, T. G., Ed.; Oxford
Press: Oxford, 1999. (b) Organoselenium Chemistry, In
Topics in Current Chemistry, Vol. 208; Wirth, T., Ed.;
Springer: Berlin, 2000.
(9) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
(10) The copper-catalyzed reaction of bromobenzene with
diphenyl disulfide produced only a 34% yield of diphenyl
sulfide. See ref. 7a.
(13) Magnesium was used instead of zinc for the reaction with
2-bromothiophene.
(14) Adapa et al. reported the stoichiometric coupling reaction
between aryl bromides with diphenyl diselenides using
CsOH. See: Varala, R.; Ramu, E.; Adapa, S. R. Bull. Chem.
Soc. Jpn. 2006, 79, 140.
(15) The Se–Se bond in diphenyl diselenide was reductively
cleaved by low valent indium and the generated
selenoindium species react with alkyl halides (not aryl) to
give alkyl aryl selenides. See: (a) Ranu, B. C.; Mandal, T.;
Samanta, S. Org. Lett. 2003, 5, 1439. (b) Ranu, B. C.;
Mandal, T. J. Org. Chem. 2004, 69, 5793.
(16) The ruthenium-catalyzed coupling reaction of diphenyl
diselenide with alkyl halides in the presence of zinc has been
reported, where cleavage of the Se–Se bond takes place. See:
Zhao, X.; Yu, Z.; Yan, S.; Wu, S.; Liu, R.; He, W.; Wang, L.
J. Org. Chem. 2005, 70, 7338.
Synlett 2006, No. 13, 2145–2147 © Thieme Stuttgart · New York