Affiliation:
1. Department of Chemistry Indian Institute of Technology Delhi Hauz Khas New Delhi 110016 India
Abstract
AbstractA Friedel‐Crafts alkylation of electron‐deficient arenes with aldehydes through ′′catalyst activation′′ is presented. Through hydrogen bonding interactions, the solvent 1,1,1,3,3,3, ‐hexafluoroisopropanol (HFIP) interacted with the added Brønsted acid catalyst pTSA•H2O, increasing its acidity. This activated catalyst enabled the Friedel–Crafts alkylation of electron‐neutral as well as electron‐deficient arenes. Strongly electron withdrawing arenes including arenes with multiple halogen atoms, NO2, CHO, CO2R, and CN, groups acted as efficient nucleophiles in this reaction. DFT studies reveal multiple roles of solvent HFIP viz; increasing the Brønsted acidity of the catalyst pTSA•H2O, and stabilization of the transition states through a concerted pathway enabling the challenging reaction.
Funder
Science and Engineering Research Board
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
9 articles.
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