Thioester Synthesis From Aldehydes and Its Derivatization to New C─O and C─N Bonds

A benign approach for the thioesterification of aldehydes to novel thioesters has been achieved in a water-mediated condition. Exploring thioester for direct esterification and amidation findings that are simple and use readily available substrates and reagents may complement existing methodologies. Thioester's direct esterification and amidation are achieved without using toxic and hazardous reagents and with minimal waste production. Significantly, direct amidation of thioester was exploited to achieve diverse primary, secondary, and tertiary amides derived from various electron-rich, electron-deficient amines.

Abstract

An efficient approach for the thioesterification of aldehydes to novel thioesters has been achieved in mild reaction conditions. Exploring thioester for direct esterification and amidation findings that are simple and use readily available substrates and reagents may complement existing methodologies. Esters and amides are the most prevalent molecules in natural compounds and industrial products. The presented protocol is significant as methods so far developed for synthesizing esters and amides employ harsh reaction conditions and hazardous coupling reagents, which pose a challenging waste management. The direct esterification and amidation of thioester are achieved without using toxic and hazardous reagents and with minimal waste production. Significantly, direct amidation of thioester was exploited to achieve diverse primary, secondary, and tertiary amides derived from various electron-rich, electron-deficient amines. It is noteworthy that different amino ester and amino alcohol derivatives also participated in the direct amidation reaction and delivered the corresponding amides in good yields. The presented method demonstrates the thioester precursor as a versatile option for synthesizing esters, amides.

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