Efficient synthesis of trifluoromethylated dihydrochalcones, aryl vinyl ketones and indanones by superelectrophilic activation of 4,4,4-trifluoro/3-(trifluoromethyl)crotonic acids

• Published in: Journal of fluorine chemistry 2012-11, Vol.143, p.292-302
• Main Authors: Surya Prakash, G.K., Paknia, Farzaneh, Narayanan, Arjun, Rasul, Golam, Mathew, Thomas, Olah, George A.
• Format: Article
• Language: English
• Subjects: Ab initio theory; Acylation/cyclialkylation; Crotonic acid; Friedel–Crafts reaction; Trifluoromethyl dihydrochalcones; Trifluoromethylindanones
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2012.07.008

Direct synthesis of trifluoromethylated dihydrochalcones, aryl vinyl ketones, and indanones has been achieved by superelectrophilic activation of 4,4,4-trifluoro/3-(trifluoromethyl)crotonic acids followed by Friedel–Crafts alkylation/acylation/cyclalkylation in excess triflic acid. [Display omitted] ► Superacid catalyzed electrophilic substitution of arenes using 4,4,4,-trifluoro/3-trifluoromethylcrotonic acids has been investigated. ► Synthesis of various trifluoromethylated dihydrochalcones, aryl vinyl ketones and indanones has been achieved. ► Position of the trifluoromethyl group seems to have profound effect on the nature of the reaction and the products. ► Mechanistic aspects have been supported by ab initio calculations. Superacid catalyzed electrophilic substitution of arenes using 4,4,4,-trifluoro/3-trifluoromethylcrotonic acids has been investigated. The direct synthesis of various trifluoromethylated dihydrochalcones, aryl vinyl ketones and indanones has been achieved by this methodology. It has been found that the position of the trifluoromethyl group has a profound effect on the nature of the reaction and the products. In the pharmaceutical industry, many fluoroorganics are shown to possess significant biological and therapeutic activities. Therefore, these novel compounds can be considered key intermediates for the preparation of potential biologically active molecules.