title: Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.
abstract: Indanones and coumarins are important intermediates for the convenient synthesis of many pharmaceutical and biologically active compounds. Fluoroorganics play a vital role in the design of very effective therapeutics due to significant enhancenment in their lipophilicity, bioavailability, and fast uptake by the presence of fluorine in these molecules. Herein, we report an efficient one-pot synthesis of trifluoromethylated arylpropanoic acids, indanones, and dihydrocoumarins using Friedel-Crafts alkylation or tandem Friedel-Crafts alkylation-cycloacylation of arenes/phenols with 2-(trifluoromethyl)acrylic acid under superacidic conditions using trifluoromethanesulfonic acid. The results have been rationalized by the structure energy calculations of the involved reaction intermediates using ab initio theoretical methods.
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA. gprakash@usc.edu
authors.forename: G K Surya
authors.initials: GK
authors.lastname: Prakash
authors.forename: Farzaneh
authors.initials: F
authors.lastname: Paknia
authors.forename: Habiba
authors.initials: H
authors.lastname: Vaghoo
authors.forename: Golam
authors.initials: G
authors.lastname: Rasul
authors.forename: Thomas
authors.initials: T
authors.lastname: Mathew
authors.forename: George A
authors.initials: GA
authors.lastname: Olah
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000478:Alkylation; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C411824:2-(trifluoromethyl)acrylic acid; D000179:Acrylates; D003374:Coumarins; D007189:Indans; D011422:Propionates