Effect of Microwave Irradiation on Friedel-Crafts Diphenylmethylation of Arenes
- 1 Department of Applied Chemistry, Ritsumeikan University, Shiga, Japan
- 2 Department of Applied Chemistry, Ritsumeikan University, Shiga, Japan
Abstract
The reaction between diphenylmethanols and substituted benzenes is useful to yield triarylmethane derivatives which are important skeletons in various functional materials and biologically relevant substances. The Reactions were carried out under microwave irradiation as environmentally-friendly method. In cyclohexane, the reaction was accelerated under microwave irradiation as compared to under conventional heating. Also, when more than 0.8 equivalents of iron(III) chloride were used, the acceleration was observed. Notably, when iron(III) chloride and arenes were combined, the temperature of the reaction solution rose to 40 ° C. It is considered that a chemical species was formed upon coordination of iron(III) chloride to the diphenylmethanols or arenes.
- Chen, P., Chen, S., Hsu. C. and Chen, C. (2016) Modeling the Global Relationships among Economic Growth, Energy Consumption and CO2 Emissions. Renewable & Sustainable Energy Reviews, 65, 420-431. https://doi.org/10.1016/j.rser.2016.06.074
- Wang, C., Zhao, D., Tsutsumi, A. and You, S. (2017) Sustainable Energy Technologies for Energy Saving and Carbon Emission Reduction. Applied Energy, 194, 223-224. https://doi.org/10.1016/j.apenergy.2017.02.045
- Kappe, C.O. (2004) Controlled Microwave Heating in Modern Organic Synthesis. Angewandte Chemie International Edition, 43, 6250-6284. https://doi.org/10.1002/anie.200400655
- Hoz, A., Diaz-Ortiz, A. and Moreno, A. (2005) Microwave in Organic Synthesis; Thermal and Non-Thermal Microwave Effects. Chemical Society Reviews, 34, 164-178. https://doi.org/10.1039/B411438H
- Clarke, R., Leonessa, F., Welch. J.N. and Skaar, T.C. (2001) Cellular and Molecular Pharmacology of Antiestrogen Action and Resistance. Pharmacological reviews, 53, 25-72.
- Rueping, M., Nachtsheim, B.J. and Ieawsuwan, W. (2006) An Effective Bismuth-Catalyzed Benzylation of Arenes and Heteroarenes. Advanced synthesis & catalysis, 348, 1033-1037. https://doi.org/10.1002/adsc.200606068
- Sun, H., Li, B., Chen, S., Li, J. and Hua, R. (2007) An Efficient Synthesis of Unsymmetrical Diarylmethanes from the Dehydration of Arenes with Benzyl Alcohols Using InCl 3 .4H2O/acetylacetone Catalyst System. Tetrahedron, 63, 10185-10188. https://doi.org/10.1016/j.tet.2007.07.093
- Shirakawa, S. and Kobayashi, S. (2007) Surfactant-Type Bronsted Acid Catalyzed Dehydrative Nucleophilic Substitutions of Alcohols in Water. Organic Letters, 9, 311-314. https://doi.org/10.1021/ol062813j
- Mertins, K., Iovel, I., Kischel, J., Zapf, A. and Beller, A. (2005) Transition-Metal-Catalyzed Benzylation of Arenes and Heteroarenes. Angewandte Chemie International Edition, 44, 238-242. https://doi.org/10.1002/anie.200460666
- Bandini, M., Tragni, M. and Umani-Ronchi, A. (2009) Iron(III)-Catalyzed Intramolecular Friedel-Crafts Alkylation of Electron-Deficient Arenes with π-Activated Alcohols. Advanced Synthesis & Catalysis, 351, 2521-2524. https://doi.org/10.1002/adsc.200900441
- Iovel, I., Mertins, K., Kischel, J., Zapf, A. and Beller, M. (2005) An Efficient and General Iron-Catalyzed Arylation of Benzyl Alcohols and Benzyl Carboxylates. Angewandte Chemie International Edition, 44, 3931. https://doi.org/10.1002/anie.200462522