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Published on: June 21, 2017
Re2O7-Catalyzed Intermolecular Dehydrative Friedel-Crafts Reaction of Aliphatic Alcohols
Qing Huang1, Yao Xiang1, Yuzhu Zheng1
1Hubei Key Laboratory of Bioinorganic Chemistry and Materia Medica, Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education; Hubei Key Laboratory of Materials Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China.
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In this paper, we describe an operationally facile and generally applicable intermolecular dehydrative Friedel-Crafts reaction for aliphatic alcohols via Re2O7 catalysis in hexafluoroisopropanol (HFIP). This method obviates the need for highly corrosive Brønsted acids or strong Lewis acids; therefore, it is convenient to perform and offers improved functional group tolerance. DFT calculations suggested that the hydrogen-bonding interactions between HFIP and the perrhenate moiety significantly lowered the energetic barrier for catalytic C-O bond cleavage in aliphatic alcohols.
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