Subscribe to RSS
DOI: 10.1055/s-2006-949607
Palladium-Catalyzed Coupling Reaction of Diaryl Dichalcogenide with Aryl Bromide Leading to the Synthesis of Unsymmetrical Aryl Chalcogenide
Publication History
Publication Date:
09 August 2006 (online)
Abstract
An efficient cross-coupling reaction of diphenyl disulfide or diselenide with substituted aryl bromides using PdCl2(dppf) and zinc has been developed. This method gave functionalized unsymmetrical aryl sulfides and selenides in good to excellent yields under neutral conditions.
Key words
sulfur - selenium - palladium - cross-coupling - catalysis
-
1a
Kondo T.Mitsudo T.-A. Chem. Rev. 2000, 100: 3205 -
1b
Ley SV.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 -
2a
Solladie G. Synthesis of Sulfides, Sulfoxides and Sulfones Vol. 6: Pergamon Press; Oxford: 1991. p.133-170 -
2b
Baird CP.Rayner CM. J. Chem. Soc., Perkin Trans. 1 1998, 1973 -
2c
Procter DJ. J. Chem. Soc., Perkin Trans. 1 1999, 641 -
2d
Procter DJ. J. Chem. Soc., Perkin Trans. 1 2000, 835 -
2e
Procter DJ. J. Chem. Soc., Perkin Trans. 1 2001, 335 - For examples of the copper-catalyzed coupling reaction, see:
-
3a
Bates CG.Gujadhur RK.Venkataraman D. Org. Lett. 2002, 4: 2803 -
3b
Kwong FY.Buchwald SL. Org. Lett. 2002, 4: 3517 -
3c
Wu Y.-J.He H. Synlett 2003, 1789 -
3d
Deng W.Zou Y.Wang Y.-F.Liu L.Guo Q.-X. Synlett 2004, 1254 - 4 For an example of the nickel-catalyzed coupling reaction, see:
Takagi K. Chem. Lett. 1987, 2221 - For examples of the palladium-catalyzed coupling reaction, see:
-
5a
Kosugi M.Shimizu T.Migita T. Chem. Lett. 1978, 13 -
5b
Migita T.Shimizu T.Asami Y.Shiobara J.-i.Kato Y.Kosugi M. Bull. Chem. Soc. Jpn. 1980, 53: 1385 -
5c
Zheng N.McWilliams JC.Fleitz FJ.Armstrong JD.Volante RP. J. Org. Chem. 1998, 63: 9606 -
5d
Schopfer U.Schlapbach A. Tetrahedron 2001, 57: 3069 -
5e
Li GY.Zheng G.Noonan AF. J. Org. Chem. 2001, 66: 8677 -
5f
Li GY. Angew. Chem. Int. Ed. 2001, 40: 1513 -
5g
Li GY. J. Org. Chem. 2002, 67: 3643 -
5h
Itoh T.Mase T. Org. Lett. 2004, 6: 4587 -
5i
Fernãndez-Rodríguez MA.Shen Q.Hartwig JF. J. Am. Chem. Soc. 2006, 128: 2180 - 6
Herradura PS.Pendola KA.Guy RK. Org. Lett. 2000, 2: 2019 -
7a
Taniguchi N. J. Org. Chem. 2004, 69: 6904 -
7b
Taniguchi N.Onami T. Synlett 2003, 829 -
7c
Taniguchi N.Onami T. J. Org. Chem. 2004, 69: 915 -
7d
Millois C.Diaz P. Org. Lett. 2000, 2: 1705 - For examples, see:
-
8a
Organoselenium Chemistry: A Practical Approach in Chemistry
Back TG. Oxford Press; Oxford: 1999. -
8b
Organoselenium Chemistry, In Topics in Current Chemistry
Vol. 208:
Wirth T. Springer; Berlin: 2000. - 9
Ajiki K.Hirano M.Tanaka K. Org. Lett. 2005, 7: 4193 - 14 Adapa et al. reported the stoichiometric coupling reaction between aryl bromides with diphenyl diselenides using CsOH. See:
Varala R.Ramu E.Adapa SR. Bull. Chem. Soc. Jpn. 2006, 79: 140 - 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:
-
15a
Ranu BC.Mandal T.Samanta S. Org. Lett. 2003, 5: 1439 -
15b
Ranu BC.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
References and Notes
The copper-catalyzed reaction of bromobenzene with diphenyl disulfide produced only a 34% yield of diphenyl sulfide. See ref. 7a.
11Typical 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.
12The reaction with p-iodonitrobenzene proceeded to give the corresponding aryl sulfide in 82% yield.
13Magnesium was used instead of zinc for the reaction with 2-bromothiophene.