A new entry to o,o’-dihalogenated deoxybenzoins by palladium-catalyzed α-arylation of 2'-chloroacetophenones

Mónica Carril,Raul Sanmartin,Esther Domínguez,Imanol Tellitu,Christian V Stevens

doi:10.3998/ark.5550190.0008.423

Abstract

The palladium-catalyzed arylation reaction is a valid, advantageous tool for the construction of o,o'-dihalo-1,2-diarylethanones. After an exhaustive range of assays the arylation of 2'- chloroacetophenones is performed in good yields, thus overcoming the handicap imposed by the presence of the ortho-chloro substituent and controlling the regioselective monoarylation with dibromoarenes.

Highlights

The extensive use of 1,2-diarylethanones or deoxybenzoins over the last decades as versatile building blocks of a whole range of compounds[1] has promoted a search for efficient ways for their preparation
Led by the classical Friedel-Crafts arylation of arylacetic acid derivatives, several methodologies have been developed for this purpose, providing a good amount of alternatives available to the synthetic chemist
When the nature of the functional groups attached to the aromatic moieties of deoxybenzoins is labile or sensitive to the reaction conditions, or when specific functionalization of ortho and/or ortho' positions is required, most of the above procedures fail.[2]

Summary

Introduction

The extensive use of 1,2-diarylethanones or deoxybenzoins over the last decades as versatile building blocks of a whole range of compounds[1] has promoted a search for efficient ways for their preparation.

Results

Conclusion