Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

Transition-Metal-Free, Potassium tert-butoxide-mediated Direct Synthesis of Symmetrical Diaryldichalcogenides from Aryl Halides

Document Type : Research Article

Authors
Mohammad Soleiman Beigi 1
fatemeh sadeghizadeh 2
fariba mohammadi 2
1 Department of Chemistry, Ilam University, Ilam, I.R. IRAN
2 Department of Chemistry, Basic of Sciences Faculty, Ilam University, PO Box 69315-516, Ilam, Iran
Abstract
In continuation of our efforts on the synthesis of diaryl disulfide compounds using coupling reactions and try to finding efficient, simple, and general methods for the direct synthesis of C-X (S, Se, Te)  bonds,  In this work,  for the first time a transition-metal-free synthesis of diaryl dichalcogenides has been reported. Potassium t-Butoxide can efficiently promote the coupling reaction of aryl halides (and-OTS) with elemental S, Se, and Te powder in DMSO without the aid of transition metal catalysts. Under the optimal conditions, a series of symmetrical diaryldisulfide, diaryldiselenide, and diarylditelluride were obtained in good to excellent yield.
Keywords
Diaryl dichalcogenides
Disulfide
Diselenide
Ditelluride
Potassium tert-butoxide
Radical

Subjects

[1] Liotta D., Monahan R., Selenium in Organic Synthesis, Science, 231: 356-361 (1986).
[2] Cremlyn R.J.W., "An Introduction to Organosulfur Chemistry", John Wiley & Sons Inc, (1996).
[3] Oae S., "Organic chemistry of Sulfur", Springer Science & Business Media, (2012).
[4] Hsieha P-A., Badsara S.S., Tsai Ch-H., Reddy D.M., Lee Ch-F., Peracetic Acid Mediated sp2 C–H Selenation of Arenes, Synlett, 27: 1557-1562 (2016).
[5] Mukherjee A.J., Zade S.S., Singh H.B., Sunoj R.B.,Organoselenium Chemistry: Role of Intramolecular Interactions, Chem. Rew, 110: 4357-4416 (2010).
[6] Derek W.J., Risto L., "Selenium and Tellurium Chemistry-From Small Molecules to Bio Molecules and Materials", Springer-Verlag, Berlin/Heidelberg, (2011).
[7] Savegnago L., Antinociceptive Properties of Diphenyl Diselenide: Evidence for the Mechanism of Action, Eur. J.Pharmacol., 555: 129-138 (2007).
[8] Ibrahim M., Hassan W., Meinerz D.F., Santos M., Klimaczewski C., Deobald A., Costa M.S., Nogueira C.W., Barbosa N.B., Rocha J.B., Antioxidant Properties of Diorganoyl Diselenides and Ditellurides: Modulation by Organic Aryl or Naphthyl Moiety, Mol. Cell. Biochem, 371: 97-104 (2012).
[9] Savegnago L., Antisecretory and Antiulcer Effects of Diphenyl Diselenide, Environ Toxicol Pharmacol, 21: 86-92 (2006).
[10] Sevier C.S., Kaiser C.A., Formation and Transfer of Disulphide Bonds in Living Cells, Nat. Rev. Mol. Cell. Bio, 3: 836-847 (2002).
[11] Jones R.C., Katritzky A.R., "Comprehensive Organic Functional Group Transformations II: Carbon with Two Attached Heteroatoms with at Least One Carbon-to-heteroatom Multiple Link", Elsevier, (2005).
[12] Saito G., Swanson J.A., Lee K-D., Drug Delivery Strategy Utilizing Conjugation via Reversible Disulfide Linkages: Role and Site of Cellular Reducing Activities, Adv. Drug. Deliv. Rev., 55: 199-215 (2003).
[13] Masel R.I., "Chemical Kinetics and Catalysis", Wiley Interscience: New York, (2001).
[14] Behr A., "Organometallic Compounds and Homogeneous Catalysis: Ullmann’s Encyclopedia of Industrial Chemistry", Wiley-VCH: Weinheim, (2002).
[15] Elschenbroich C., "Organometallics", Wiley-VCH: Weinheim, (2006).
[16] Brase S., de Meijere A., "Metal-Catalyzed Cross-Coupling Reactions", 2nd ed., de Meijere, A., Diederich, F., (Eds), Wiley-VCH: Weinheim, (2004).
[17] Mandal B., Basu B., Recent Advances in S–S Bond Formation, RSC Adv, 4: 13854-13881 (2014).
[18] Singh D., Deobald A.M., Camargo L.R.S., Tabarelli G., Rodrigues O.E.D., Braga A.L., An Efficient One-Pot Synthesis of Symmetrical Diselenides or Ditellurides from Halides with CuO Nanopowder/Se0 or Te0/Base, Org. Lett, 12: 3288-3291 (2010).
[19] Krief A., Delmotte C., Colaux-Castillo C., Reactions Involving Inorganic Compounds, Pure. Appl. Chem, 72: 1709-1713 (2000).
[20] Ruano J.L.G., Parra A., Alemán J., Efficient Synthesis of Disulfides by Air Oxidation of Thiols under Sonication. Green Chem., 10: 706 -711(2008).
[21] Gholinejad M.,  Firouzabadi H., One-Pot Odorless Thia-Michael Reaction by Copper Ferrite Nanoparticle-Catalyzed Reaction of Elemental Sulfur, Aryl Halides and Electron-Deficient Alkenes, New J. Chem., 39: 5953-5959 (2015).
[22] Gholinejad M., One‐Pot Synthesis of Symmetrical Diaryl Trithiocarbonates through Copper‐Catalyzed Coupling of Aryl Compounds, Sodium Sulfide, and Carbon Disulfide, Eur. J. Org. Chem, 2013: 257 -259 (2013).
[23] Firouzabadi H., Iranpoor N., Gholinejad M., Samadi A., Copper(I) Iodide Catalyzes Odorless Thioarylation of Phenolic Esters with Alkyl Derivatives Using Thiourea In Wet Polyethylene Glycol (PEG 200), Journal of Molecular Catalysis A: Chemical, 377: 190-196 (2013).
[24] Reeves J.T., Camara K., Han Z.S., Xu Y., Lee H., Busacca C.A., Senanayake C. H., The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides, Org. Lett., 16: 1196 -1199 (2014).
[25]  Firouzabadi H., Iranpoor N., Gholinejad M., One‐Pot Thioetherification of Aryl Halides Using Thiourea and Alkyl Bromides Catalyzed by Copper(I) Iodide Free from Foul‐Smelling Thiols in Wet Polyethylene Glycol (PEG 200), Adv. Synth. Catal, 352: 119-124 (2010). 
[26] Soleiman-Beigi M., Arzehgar Z., An Efficient One-Pot Method for the Direct Synthesis  of Organic Disulfides from Aryl/Alkyl Halides in the Presence of CuCl Using Morpholin-4-ium Morpholine-4-Carbo-Dithioate , J. Sulfur. Chem., 36: 395-402 (2015).
[27] Ming-De R., Huo-Rong Zh., Wio-Qiang F., Xun-Jun Zh., First Example of Selenium Transfer Reaction of Primary Selenoamides and Selenourea. Novel Synthesis of Dialkyl Diselenides from Alkyl Halides, J. Organometallic. Chem, 485: 19-24 (1995).
[28] Ke F., Qu Y., Jiang Z., Li Z., Wu D., Zhou X., An Efficient Copper-Catalyzed Carbon−Sulfur Bond Formation Protocol in Water, Org. Lett, 13: 454 -457 (2011).
[29] Soleiman-Beigi M., Yavari I., Sadeghizadeh F., The Direct Synthesis of Symmetrical Disulfides and Diselenidesby Metal-Organic Framework MOF-199 as an Efficient Heterogenous Catalyst, RSC Adv, 5: 87564-87570 (2015).
[30] Soleiman-Beigi M., Mohammadi F., Metal Organic Framework 199- Catalyzed Domino Sulfur-Coupling and Transfer Reactions: The Direct Synthesis of Symmetric Diaryl Disulfides from Aryl Halides, Catt. Lett., 146:1497-1504 (2016).
[31] Soleiman-Beigi M., Arzehgar Z., Ni‐Catalyzed Cross‐Coupling Reaction: The Direct Synthesis of Symmetrical Disulfanes from Aryl and Primary Alkyl Halides, Heteroatom Chem., 26: 355-360 (2015).
[32] Soleiman-Beigi M., Mohammadi F., A Novel Nickel-Catalyzed Domino Method for the Direct Synthesis of Symmetrical Disulfides Using Potassium 5-Methyl-1,3,4-oxadiazole-2-thiolate as a Sulfurating Reagent, Synlett., 26: 911-914 (2015).
[33] Soleiman-Beigi M., Hemmati M., An Efficient, One-Pot and CuCl-Catalyzed Route to the Synthesis of Symmetric Organic Disulfides via Domino Reactions of Thioacetamide and Aryl (Alkyl) Halides, Appl. Organometal. Chem, 27: 734-736 (2013). 
[34] Soleiman-Beigi M., Mohammadi F., A Novel Copper-Catalyzed, One-Pot Synthesis of Symmetric Organic Disulfides from Alkyl and Aryl Halides: Potassium 5- Methyl-1, 3, 4-Oxadiazole-2-Thiolate as a Novel Sulfur Transfer Reagent, Tetrahedron Lett., 53:7028-7030 (2012).
[35] Botteselle G.V., Godoi M., Galetto F.Z., Bettanin L., Singh D., Rodrigues O.E.D., Braga A.L., Microwave-Assisted One-Pot Synthesis of Symmetrical Diselenides, Ditellurides and Disulfides from Organoyl Iodides and Elemental Chalcogen Catalyzed by CuO Nanoparticle, Journal of Molecular Catalysis A, 365: 186- 193(2012).
[36] Li Z., Ke, F., Deng H., Xu H., Xianga H., Zhou X., Synthesis of Disulfides and Diselenides by Copper Catalyzed Coupling Reactions in Water, Org. Biomol. Chem, 11: 2943-2946 (2013).
[37] Kassaee M.Z., Motamedi E., Movassagh B., Poursadeghi S., Iron-Catalyzed Formation of C–Se and C–Te Bonds through Cross-Coupling of Aryl Halides with Se(0) and Te(0)/Nano-Fe3O4@GO, Synthesis, 45: 2337-2342 (2013).
[38] Sun Ch-L., Sh Zh-j., Transition-Metal-Free Coupling Reactions, Chem. Rev, 114:9219-9280 (2014). 
[39] Fukuoka Sh., Transition Metal Catalyst-Free and Radical Initiator-Free Carbonylation of Aryl Iodides, Ind. Eng. Chem. Res, 55: 4830-4835 (2016).
[40] Bu M-j., Lu G-p., Cia Ch., Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert-Butyl Nitrite, Synlett, 26: 1841-1846 (2015).
[41] Pandya V.G., Mhaske S.B., Transition-Metal-Free C–S Bond Formation: A Facile Access to Aryl Sulfones from Sodium Sulfinates via Arynes, Org. Lett., 16: 3836-3839(2014).
[42] MehtaV. P., Punji B., Recent Advances in Transition-Metal-Free Direct C–C and C–heteroatom Bond Forming Reactions, RSC Adv., 3: 11957-11986 (2013).
[43] Zou L- H., Reball J., Mottweiler J., Bolm C., Transition Metal-Free Direct C–H Bond Thiolation of 1,3,4-oxadiazoles and Related Heteroarenes, Chem. Commun, 48: 11307-11309 (2012).
[44] Thome I., Bolm C., Transition-Metal-Free Intramolecular N-Arylations, Org. Lett., 14, p. 1892-1895 (2012).
[45] Roman D.S., Takahashi Y., Charette  A.B., Potassium tert-Butoxide Promoted Intramolecular Arylation via a Radical Pathway, Org. let., 13: 3242-3245 (2011).
[46] Dong Y., Lipschutz M.I., Tilley T.D., Regioselective, Transition Metal-Free C–O Coupling Reactions Involving Aryne Intermediates, Org. Lett, 18: 1530-1533 (2016).
[47] Huang P., He B-Y., Wang H.M., Lu J-M., Transition-Metal-Free, Potassium tert-Butoxide/Dimethyl Sulfoxide Mediated Amination between Tertiary Amines and Aryl Halides, Synthesis, 47: 221 -227(2015).
[48] Kumar A., Bhakuni B.S., Prasad Ch.D., Kumar Sh., Kumar S., Potassium tert-butoxide-mediated Synthesis of Unsymmetrical Diaryl Ethers, Sulfides and Selenides from Aryl Bromides, Tetrahedron, 69: 5383-5392 (2013).
[49] Bajracharya G.B., Daugulis O., Direct Transition-Metal-Free Intramolecular Arylation of Phenols, Org. Lett, 10: 4625-4628 (2008).
[50] Ghosh S., De S., Kakde B.N., Bhunia S., Adhikary A., Bisai A., Intramolecular Dehydrogenative Coupling of sp2 C–H and sp3 C–H Bonds: An Expeditious Route to 2-Oxindoles, Org. Lett, 14: 5864-5867 (2012).
[51] Shirakawa E., Itoh K-I., Higashino T., Hayashi T., tert-Butoxide-Mediated Arylation of Benzene with Aryl Halides in the Presence of a Catalytic 1,10-Phenanthroline Derivative, J. Am. Chem. Soc, 132: 15537-15539 (2010).
[52] Shirakawa E., Zhang X., Hayashi T., Mizoroki–Heck‐Type Reaction Mediated by Potassium tert‐Butoxide, Angew. Chem., Int. Ed, 50: 4671-4674 (2011).
[53] Sun C.-L., Li H., Yu D-G., Yu M., Zhou X., Lu X-Y., Huang K., Zheng S-F., Li B-J., Shi Z-J.,An Efficient Organocatalytic Method for Constructing Biaryls Through Aromatic C-H Activation, Nat. Chem, 2: 1044-1049 (2010).
[54] Arguello J.E., Schmidt L.C., Penenory A.B., “One-Pot” Two-Step Synthesis of Aryl Sulfur Compounds by Photoinduced Reactions of Thiourea Anion with Aryl Halides, Org. Lett, 5: 4133 (2003).
[55] Studer A., Curran D.P., Organocatalysis and C-H Activation Meet Radical‐ and Electron‐Transfer Reactions, Angew. Chem. Int. Ed, 50: 5018-5022 (2011).
[56] Yanagisawa S., Itami K., tert‐Butoxide‐Mediated C-H Bond Arylation of Aromatic Compounds with Haloarenes, Chem. Cat. Chem., 3: 827-829 (2011).
[57] Barham j.P, Coulthard G., Emery J.K., Doni E., Cumine F., Nocera G., John P.M., Berlouis E.A.L., McGuire T., Tuttle T., Murphy A.A.,KOtBu: A Privileged Reagent for Electron Transfer Reactions?, J. Am. Chem. Soc., 138: 7402-7410 (2016).
[58] Liu W., Cao H., Zhang H., Zhang H., Chang K.H., Hi Ch., Wang H., Kwong F.W., Lei A., Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C−H Arylation of Unactivated Benzene, J. Am. Chem. Soc., 132:16737-16740 (2010).