HFIP-promoted Para-Selective Alkylation of Anilines and Phenols with Tertiary Alkyl Bromides
ORGANIC CHEMISTRY FRONTIERS(2023)
摘要
A hexafluoroisopropanol-promoted highly regioselective Friedel-Crafts alkylation of arenes has been developed in this study. Various arenes, including anilides, anisoles, and phenols, were compatible with the reaction, leading to para-alkylated products in moderate to excellent yields. Preliminary mechanistic studies revealed that HFIP acted as a weak Lewis acid to activate haloalkanes and coordinated with arenes through hydrogen bonding to increase the steric hindrance of the coordinated functional group, affording a highly para-selective alkylated product.
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