Friedel–Crafts alkylation with α-bromoarylacetates for the preparation of enantioenriched 2,2-diarylethanols

Abstract

Highly enantioenriched 2,2-diarylethanols can be efficiently synthesized using the AgOTf-promoted Friedel–Crafts alkylation of (hetero)arenes with configurationally labile α-bromoarylacetates.

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

“…Over the past decades, numerous elegant methods have been developed to construct these versatile units through different coupling transformations (Scheme a). The conventional Friedel–Crafts or UV-irradiated alkylation of arenes with alkyl α-haloacetates and benzyne-promoted transformations gives access to a mixture of regioisomers. The utilization of a noble-metal catalyst, for now at least, is inevitable in catalytic carbonylation reactions .…”

Facile Friedel–Crafts alkylation of arenes under solvent-free conditions

“…Diarylacetates are widely present in natural products, 1 pharmaceuticals, 2 and building blocks of complex molecules. 3 Therefore, the synthesis of diarylacetates has received considerable attention over the past few decades, including the α-arylation of arylacetates with aryl halides, 4 Friedel–Crafts alkylation of α-bromoarylacetates with arenes, 5 and the reaction of arenes with α-aryl-α-diazoesters. 6 Among these, the reaction of arenes with α-aryl-α-diazoesters represents a straightforward route to diarylacetates and has received much attention in the past decade.…”

Selective alkylation of mandelic acid to diarylacetic acids over a commercial zeolite

“…Pd plus ligand 18,19 ), atom inefficient ( e.g. stoichiometric metal salts 20,21 or halogenated substrates 18–21 ) and/or hazardous to implement (diazo-precursors 22–24 ).…”