One-Step Synthesis of 1-Chloro-3-arylacetone Derivatives from Arylacetic Acids

Abstract

A practical one-step method has been developed to prepare α-chloroketones from readily available, inexpensive phenylacetic acid derivatives. The method utilizes the unique reactivity of an intermediate Mg-enolate dianion, which displays selectivity for the carbonyl carbon of chloromethyl carbonyl electrophiles. Decarboxylation of the intermediate occurs spontaneously during the reaction quench. The utility of the reaction products has been demonstrated through the total synthesis of the natural product cimiracemate B.

Design, synthesis and modelling of photoreactive chemical probes for investigating target engagement of plasmepsin IX and X in Plasmodium falciparum

“…35 According to work performed by M. J Zacuto et al, it is important that in this step the reaction mixture is added to the citric acid solution and not the other way around as it prevents Mg salt precipitation which would complicate the work-up procedure. 36 Fig. 3 Design of benzophenone probes 20a-20d for synthesis and biological activity evaluation in P. falciparum.…”

Palladium-Catalyzed Acylation Strategies and Their Applications Towards Biologically Relevant Products

“…It is also worth noting that ketones are regarded as important synthons in organic chemistry because of their electrophilic properties. Traditional methods for synthesizing ketones include: (a) organometallic 1,2-additions to Weinreb amides, [40][41][42][43][44] (b) Friedel-Crafts acylation, 45,46 and (c) Barbier/Grignard reactions with aldehydes followed by oxidation. [47][48][49] All the above-developed strategies are associated with limitations, e.g., they are unsuitable for the selective functionalization of certain electron-deficient arene substrates and those flanked by sensitive functional groups This document was downloaded for personal use only.…”