弗里德尔-克拉夫茨反应
催化作用
烷基化
化学
溶剂
亲核细胞
布朗斯特德-洛瑞酸碱理论
药物化学
氢键
光化学
有机化学
分子
作者
S. P. Singh,Samrat Mondal,Vikas Tiwari,Tarak Karmakar,Chinmoy Kumar Hazra
标识
DOI:10.1002/chem.202300180
摘要
A 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•H2 O, 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, CO2 R, 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•H2 O, and stabilization of the transition states through a concerted pathway enabling the challenging reaction.
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