Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.
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.
Prakash
G K Surya
GK
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA. gprakash@usc.edu
Paknia
Farzaneh
F
Vaghoo
Habiba
H
Rasul
Golam
G
Mathew
Thomas
T
Olah
George A
GA
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
C411824:2-(trifluoromethyl)acrylic acid; D000179:Acrylates; D003374:Coumarins; D007189:Indans; D011422:Propionates