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Preparation of Trifluoromethylated Dihydrocoumarins, Indanones, and Arylpropanoic Acids by Tandem Superacidic Activation of 2-(trifluoromethyl)acrylic Acid With Arenes

Preparation of Trifluoromethylated Dihydrocoumarins, Indanones, and Arylpropanoic Acids by Tandem Superacidic Activation of 2-(trifluoromethyl)acrylic Acid With Arenes

G K Surya Prakash, Farzaneh Paknia, Habiba Vaghoo, Golam Rasul, Thomas Mathew, George A Olah

J Org Chem. 2010 Apr 2;75(7):2219-26.

PMID: 20218629

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP381986	2-(Trifluoromethyl)acrylic acid		381-98-6	Price

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