期刊
ORGANIC CHEMISTRY FRONTIERS
卷 10, 期 10, 页码 2476-2481出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3qo00342f
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A highly regioselective Friedel-Crafts alkylation of arenes was developed using hexafluoroisopropanol as a promoter. Various arenes, including anilides, anisoles, and phenols, were compatible with the reaction, yielding para-alkylated products in moderate to excellent yields. Mechanistic studies showed that hexafluoroisopropanol acted as a weak Lewis acid to activate haloalkanes and coordinated with arenes through hydrogen bonding, leading to highly para-selective alkylated products.
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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