Carbon-carbon bond formation in aqueous media. Benzamidomethylation of some carbon nucleophiles

Ana Mateska,Bozhana Mikhova,Kristina Mladenovska,Goran Stojković,Emil Popovski

doi:10.3998/ark.5550190.0010.a13

Ana Mateska, Bozhana Mikhova + Show 3 more

Open Access

https://doi.org/10.3998/ark.5550190.0010.a13

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Abstract

C-C bond formation reactions between (benzamidomethyl)triethylammonium chloride (1) and some carbon nucleophiles (2a-f) were performed smoothly in aqueous media, under mild reaction conditions and ambient temperature. Mono-C-alkyl (3a, 3b, 3c) and di-C-alkyl (3d, 3e, 3f) derivatives were obtained without using a catalyst. Crystals of the products were easily isolated by simple filtration, in moderate yields and with no apparent contamination due to the formation of O-alkyl products.

Highlights

Carbon-carbon bond formation is the essence of organic synthesis and provides the foundation for generating more complicated organic compounds from the simpler ones
Literature data for the C-C bond formation by the SN2 reactions of enolate intermediates in aqueous medium[11] are sparse. This motivated our research to be primary focused on investigating the possibility for building new C-C bonds in the reaction of nucleophilic substitution in aqueous media without using a catalyst and secondary, on the synthesis of new benzamidomethyl derivatives, which may have a great application as constituent moieties for the intermediates within the synthesis of different biologically active compounds
In this paper we present the formation of C-C bonds in the reactions of nucleophilic substitution between 1 and different carbon nucleophiles, in aqueous media, without using a catalyst

Summary

Introduction

Carbon-carbon bond formation is the essence of organic synthesis and provides the foundation for generating more complicated organic compounds from the simpler ones. Abstract C-C bond formation reactions between (benzamidomethyl)triethylammonium chloride (1) and some carbon nucleophiles (2a-f) were performed smoothly in aqueous media, under mild reaction conditions and ambient temperature. Allylic substitution of alcohols with some C-nucleophiles such as βdiketones, catalyzed by Pd - complexes, gives an excellent result for forming new C-C bonds.[3]

Results

Conclusion