Application of the Catalytic Friedel-Crafts Acylation Reaction and ­Regioselectivity Correlations

Abstract

A correlation was found between electronic properties and regioselectivity in the Friedel-Crafts reaction of substituted phenylacetic and benzoic acids with anisole, utilising substoichiometric (down to 1 mol%) amounts of catalyst. Relative reactivities of selected catalysts for this reaction were also studied.

catalysis - substituent effects - regioselectivity - Friedel-Crafts reaction - acylations

References and Notes

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5

Lewis acids: TMSOTf, Hf(OTf)₄, Yb(OTf)₃, Cu(OTf)₂, In(OTf)₃, Zn(OTf)₂, CuI, TMSI, AlCl₃, ZnCl₂, TiCl₄, BiCl₃, FeCl₃, Fe₃O₄, ZnO, Al₂O₃, Ti(Oi-Pr)₂Cl₂, Ti(Oi-Pr)₄, BF₃·OEt₂, Zn(OAc)₂, CeSO₄·8H₂O, H₃(PW₁₂O₄₀), graphite. Brønsted acids: oxalic acid, trichloroacetic acid, TFA, HCl, HBr, H₂SO₄, HNO₃, TfOH, H₃PO₄.

6 Hansch C. Leo A. Taft RW. Chem. Rev.  1991,  91:  165