IJOC  Vol.1 No.4 , December 2011
BF3.OEt2-Mediated Benzylation of Arenes and Heteroarenes with Benzyl Ether Derivatives
ABSTRACT
An efficient BF3.OEt2-promoted benzylation of arenes and heteroarenes with various benzyl ether derivatives has been developed. This method provided alternative access to valuable diarylmethane in good yields under mild conditions via an easy work-up procedure.

Cite this paper
nullL. Dang, Q. Li, T. Ma, S. Sheng and W. Zeng, "BF3.OEt2-Mediated Benzylation of Arenes and Heteroarenes with Benzyl Ether Derivatives," International Journal of Organic Chemistry, Vol. 1 No. 4, 2011, pp. 176-182. doi: 10.4236/ijoc.2011.14026.
References
[1]   M. G. Nordberg, K. Kolmodin, J. Aquist, S. F. Queemer and A. J. Hallberg, “Design, Synthiesis, Computational Prediction, and Biological Evaluation of Ester Soft Drug as Inhibitors of Dihydrofolate Reductase from Pneumocystis carinii,” Journal of Medicinal Chemistry, Vol. 44, No. 15, 2001, pp. 2391-2402. doi:10.1021/jm010856u

[2]   H. H. Sun, V. J. Paul and W. Fenical, “Avrainvilleol, a Brominated Diphenylmethane Derivative with Feeding Deterrent Properties from the Tropical Green Alga Avrainvillea Longicaulis,” Phytochemistry, Vol. 22, No. 3, 1983, pp. 743-745. doi:10.1016/S0031-9422(00)86974-5

[3]   H. Hoshina, K. Maekawa, K. Taie, T. Igarashi and T. Salurai, “A New Route to Papaverine Analogs via Photocyclization of Substituted N-Acyl-α-dehydrophen- ylalaninamides,” Heterocycles, Vol. 60, 2003, pp. 1779- 1786.

[4]   C. Manzoni, M. R. Lovati, A. Bonelli, G. Galli and C. R. Sirtori, “Differential Effects of Beclobrate on Lipid/ Lipoprotein Distribution in Normal and Hypercholesterolemic Rats,” European Journal of Pharmacology, Vol. 190, No. 1-2, 1990, pp. 39-49. doi:10.1016/0014-2999(90)94110-J

[5]   C. Rose, O. Vtoraya, A. Pluzanska, N. Davidson, M. Gershanovich, R. Thomas, S. Johnson, J. Caicedo, H. Gervasio, G. Manikhas, F. B. Ayed, S. B. Radoux, H. A. C. Ross and R. Lang, “An Open Randomised Trial of Second-Line Endocrine Therapy in Advanced Breast Cancer: Comparison of the Aromatase Inhibitors Letrozole and Anastrozole,” European Journal of Cancer, Vol. 39, No. 16, 2003, pp. 2318-2327. doi:10.1016/S0959-8049(03)00630-0

[6]   V. B. Andela, “Functional Antagonism between NF-kB and Nuclear Receptors: Implications in Carcinogenesis and Strategies for Optimal Cancer Chemopreventive Interventions,” Current Cancer Drug Targets, Vol. 4, No. 4, 2004, pp. 337-344. doi:10.2174/1568009043332952

[7]   M. S. Khan, M. R. A. Al-Mandhary, M. K. Al-Suti, B. Ahrens, M. F. Mahon, L. Male, P. R. Raithby, C. E. Boothby and A. Kohler, “Synthesis, Characterisation and Optical Spectroscopy of Diynes and Poly-Ynes Con- taining Derivatised Fluorenes in the Backbone,” Dalton Transaction, Vol. 1, 2003, pp. 74-84. doi:10.1039/b208963g

[8]   S. L. You, Q. Cai and M. Zeng, “Chiral Br?nsted Acid Catalyzed Friedel-Crafts Alkylation Reactions,” Chemical Society Reviews, Vol. 38, No. 8, 2009, pp. 2190-2201. doi:10.1039/b817310a

[9]   H. M. Peng, L. X. Dai and S. L. You, “Enantioselective Palladium-Catalyzed Direct Alkylation and Olefination Reaction of Simple Arenes,” Angewandte Chemie Inter- national Edition, Vol. 49, No. 34, 2010, pp. 5826-5828. doi:10.1002/anie.201000799

[10]   S. Messaoudi, J. D. Brion and M. Alami, “Transition- Metal-Catalyzed Direct C-H Alkenylation, Alkynylation, Benzylation, and Alkylation of (Hetero) Arenes,” Euro- pean Journal of Organic Chemistry, Vol. 2010, No. 34, 2010, pp. 6495-6516. doi:10.1002/ejoc.201000928

[11]   C. Zhang, X. Gao, J. Zhang and X. Peng, “Fe/CuBr2- Catalyzed Benzylation of Arenes and Thiophenes with Benzyl Alcohols,” Synlett, Vol. 2, 2010, pp. 261-265. doi:10.1055/s-0029-1218571

[12]   W. Yao, P. makowski, C. Giordano and F. Goettmann, “Synthesis of Early-Transition-Metal Carbide and Nitride Nanoparticles through the Urea Route and Their Use as Alkylation Catalysts,” Chemistry—A European Journal, Vol. 15, No. 44, 2009, pp. 11999-12004. doi:10.1002/chem.200901496

[13]   P. Makowski, R. Rothe, A. Thomas, M. Niederberger and F. Moettmann, “Chlorine Borrowing: An Efficient Method for an Easier Use of Alcohols as Alkylation Agents,” Green Chemistry, Vo1. 11, 2009, pp. 34-37.

[14]   F. Wang and W. Ueda, “High Catalytic Efficiency of Nanostructured Molybdenum Trioxide in the Benzylation of Arenes and an Investigation of the Reaction Mechanism,” Chemistry—A European Journal, Vol. 15, No. 3, 2009, pp. 742-753. doi:10.1002/chem.200801153

[15]   M. Kitano, K. Nakajima, J. N. Kondo, S. Hayashi and M. Hara, “Protonated Titanate Nonotubes as Solid Acid Catalyst,” Journal of the American Chemical Society, Vol. 132, No. 19, 2010, pp. 6622-6623. doi:10.1021/ja100435w

[16]   P. K. Thallapally, C. A. Fernandez, R. K. Motkuri, S. K. Nune, J. Liu and C. H. F. Peden, “Micro and Mesoporous Metal-Organic Frameworks for Catalysis Applications,” Dalton Transactions, Vol. 39, No. 7, 2010, pp. 1692- 1694. doi:10.1039/b921118g

[17]   V. L. Budarin, J. H. Clark, R. Luque and D. Macquarrie, “Versatile Mesoporous Carbonaceous Materials for Acid Catalysis,” Chemical Communications, Vol. 6, 2007, pp. 634-636. doi:10.1039/b614537j

[18]   G. A. Sereda, “Alkylation on Graphite in the Absence of Lewis Acids,” Tetrahedron Letters, Vol. 45, No. 39, 2004, pp. 7265-2667. doi:10.1016/j.tetlet.2004.08.026

[19]   Y. Hashimoto, K. Hirata, H. Kagoshima, N. Kihara, M. Hasegawa and K. Saigo, “Gallium Dichloride-Mediated Reductive Friedel-Crafts Reaction,” Tetrahedron, Vol. 49, No. 27, 1993, pp. 5969-5978. doi:10.1016/S0040-4020(01)87183-0

[20]   J. M. Aizpurua, B. Lecea and C. Palomo, “Reduction of Carbonyl Compounds Promoted by Silicon Hydrides under the Influence of Trimethylsilyl-Based Reagents,” Canadian Journal of Chemistry, Vol. 64, No. 12, 1986, pp. 2342-2347. doi:10.1139/v86-386

[21]   T. Miyai, Y. Onishi and A. Baba, “Indium Trichloride Catalyzed Reductive Friedel-Crafts Alkylation of Aro- matics Using Carbonyl Compounds,” Tetrahedron Le- tters, Vol. 39, No. 35, 1998, pp. 6291-6294. doi:10.1016/S0040-4039(98)01333-1

[22]   K. Mertins, I. Iovel, J. Kischel, A. Zapf and M. Beller, “Transition-Metal-Catalyzed Benzylation of Arenes and Heteroarenes,” Angewandte Chemie International Edition, Vol. 44, 2005, pp. 238-242. doi:10.1002/anie.200460666

[23]   M. Rueping, B. J. Nachtsheim and W. Ieawsuwan, “An Effective Bismuth-Catalyzed Benzylation of Arenes and Heteroarenes,” Advanced Synthesis & Catalysis, Vol. 348, No. 9, 2006, pp. 1033-1037. doi:10.1002/adsc.200606068

[24]   A. Prades, R. Corberan, M. Poyatos and E. Peris, “A Simple Catalyst for the Efficient Benzylation of Arenes by Using Alcohols, Ethers, Styrenes, Aldehydes, or Ke- tones,” Chemistry—A European Journal, Vol. 15, No. 18, 2009, pp. 4610-4613. doi:10.1002/chem.200802740

[25]   Y. P. Xiao, X. Y. Liu and C. M. Che, “Highly Efficient Gold(III)-Catalyzed Intermolecular Hydroarylation of Unactivated Alkenes with Arenes under Mild Conditions,” Journal of Organometallic Chemistry, Vol. 694, No. 4, 2009, pp. 494-501. doi:10.1016/j.jorganchem.2008.07.035

[26]   K. M. Reddy, N. S. Babu, P. S. S. Prasad and N. Lingaiah, “Aluminium-Exchanged Tungstophosphoric Acid: An Efficient Catalyst for Intermolecular Hydroarylation of Vinyl Arenes,” Catalysis Communications, Vol. 9, No. 15, 2008, pp. 2525-2531. doi:10.1016/j.catcom.2008.07.007

[27]   I. Shiina, M. Suzuki, “The Catalytic Friedel-Crafts Alkylation Reaction of Aromatic Compounds with Benzyl or Allyl Silyl Ethers Using Cl2Si(OTf)2 or Hf(OTf)4,” Tetrahedron Letters, Vol. 43, No. 36, 2002, pp. 6391-6394. doi:10.1016/S0040-4039(02)01376-X

[28]   S. A. Ardizzone, P. Beltrame and G. Zuretti, “Kinetics of the Reaction of Toluene with Benzyl Alcohol over Sulfated Zirconia,” Applied Catalysis A: General, Vol. 314, No. 2, 2006, pp. 240-247. doi:10.1016/j.apcata.2006.08.026

[29]   J. R. Satam and R. V. Jayaram, “Liquid Phase Friedel- Crafts Benzylation of Aromatics on a Polymer-Supported 12-Tungstophosphoric Acid Catalyst,” Catalysis Communications, Vol. 9, No. 9, 2008, pp. 1937-1940. doi:10.1016/j.catcom.2008.03.018

[30]   B. Q. Wang, S. K. Xiang, Z. P. Sun, B. T. Guan, P. Hu, K. Q. Zhao and Z. J. Shi, “Benzylation of Arenes through FeCl3-Catalyzed Friedel-Crafts Reaction via C-O Activation of Benzyl Ether,” Tetrahedron Letters, Vol. 49, No. 27, 2008, pp. 4310-4312. doi:10.1016/j.tetlet.2008.04.117

[31]   N. Christoph and M. Herbert, “Kinetics of the Solvolyses of Fluoro-Substituted Benzhydryl Derivatives: Reference Electrofuges for the Development of a Comprehensive Nucleofugality Scale,” European Journal of Organic Ch- emistry, Vol. 2010, No. 8, 2010, pp. 1435-1439. doi:10.1002/ejoc.200901400

[32]   K. Tobias, V. Katja and L. Torsten, “Regioselective Arene Functionalization: Simple Substitution of Carboxylate by Alkyl Groups,” Chemistry—A European Journal, Vol. 15, No. 44, 2009, pp. 12082-12091. doi:10.1002/chem.200901774

[33]   H. B. Sun, B. Li, S. J. Chen, J. Li and R. M. Hua, “An Efficient Synthesis of Unsymmetrical Diarylmethanes from the Dehydration of Arenes with Benzyl Alcohols Using InCl3?4H2O/Acetylacetone Catalyst System,” Tetr- ahedron, Vol. 63, No. 41, 2007, pp. 10185-10188. doi:10.1016/j.tet.2007.07.093

[34]   M. Kristin, L. Irina, K. Jette and Z. Alexander, “Gold- Catalyzed Benzylation of Arenes and Heteroarenes,” Ad- vanced Synthesis & Catalysis, Vol. 348, No. 6, 2006, pp. 691-695. doi:10.1002/adsc.200505433

[35]   F. Alice, T. Amy and B. William, “Palladium-Catalyzed Cross-Coupling of B-Benzyl-9-Borabicyclo[3.3.1]nonane to Furnish Methylene-Linked Biaryls,” Organic Letters, Vol. 7, No. 22, 2005, pp. 4975-4978. doi:10.1021/ol051929x

[36]   A. Muriel and G. Corinne, “Synthesis of Functionalised Diarylmethanes via a Cobalt-Catalysed Cross-Coupling of Arylzinc Species with Benzyl Chlorides,” Chemical Communications, Vol. 40, 2008, pp. 5019-5021. doi:10.1039/b809626k

[37]   M. Kenichi, K. Takeo, S. Norio, K. Kozo, G. Takahiro and N. J. Yukinori, “Synthesis of Novel Silyl Enol Ethers from Chlorodimethyl(Naphthylphenylmethyl)silanes Hav- ing a Chiral Centre and a Ketone and Their Chirality Transfer Effects in Crossed-Aldol Reactions,” Journal of Chemical Research, Vol. 2009, No. 1, 2009, pp. 46-51. doi:10.3184/030823409X393709

[38]   C. R. Chen, S. L. Zhou and H. M. Gau, “ Extremely Efficient Cross-Coupling of Benzylic Halides with Ary- ltitanium Tris(isopropoxide) Catalyzed by Low Lo- adings of a Simple Palladium(II) Acetate/Tris(p-tolyl) phosphine System,” Advanced Synthesis & Catalysis, Vol. 352, No. 10, 2010, pp. 1718-1727. doi:10.1002/adsc.201000311

[39]   H. Nicolas, “One-Pot Dual Substitutions of Bromobenzyl Chloride, 2-Chloromethyl-6-halogenoimidazo[1,2-a] py- ridine and -[1,2-b]pyridazine by Suzuki-Miyaura Cross- Coupling Reactions,” European Journal of Organic Ch- emistry, Vol. 2008, No. 28, 2008, pp. 4824-4827. doi:10.1002/adsc.201000311

[40]   Z. K. Yu, “Synthesis and Structural Characterization of Complexes Derived from Treatment of Gallium Trichloride with 3,5-Diphenylpyrazole,” Polyhedron, Vol. 21, No. 11, 2002, pp. 1117-1123. doi:10.1016/S0277-5387(02)00931-2

[41]   T. Lloyd Fletcher and J. Blackwell, “Experiments in the Colchicine Field. VI. A Method for the Synthesis of Ring B1,” Journal of the Chemical Society, 1961, pp. 1400- 1420.

[42]   S. Jason R, L. Nicholas E, “Palladium-Catalyzed Synthesis of Diarylmethanes: Exploitation of Carbanionic Leav- ing Groups,” Organic Letters, Vol. 11, No. 12, 2009, pp. 2575-2578. doi:10.1021/ol900874z

[43]   T. Z. Nichele and A. L. Monteiro, “Synthesis of Diarylmethane Derivatives from Stille Cross-Coupling Reactions of Benzylic Halides,” Tetrahedron Letters, Vol. 48, 2007, pp. 7472-7475.

 
 
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