HFIP-promoted para-selective alkylation of anilines and phenols with tertiary alkyl bromides?
Organic Chemistry Frontiers Pub Date: 2023-04-05 DOI: 10.1039/D3QO00342F
Abstract
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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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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