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Thioesterification and Selenoesterification of Amides via Selective N–C Cleavage at Room Temperature: N–C(O) to S/Se–C(O) Interconversion
Synthesis ( IF 2.6 ) Pub Date : 2020-02-25 , DOI: 10.1055/s-0039-1690055
Md. Mahbubur Rahman , Guangchen Li , Michal Szostak 1
Affiliation  

The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles. Herein, we report an exceedingly mild method for the direct thioesterification and selenoesterification of amides by selective N–C(O) bond cleavage in the absence of transition metals. Acyclic amides undergo N–C(O) to S/Se–C(O) interconversion to give the corresponding thioesters and selenoesters in excellent yields at room temperature via a tetrahedral intermediate pathway (cf. an acyl metal).

中文翻译:

酰胺在室温下通过选择性N-C裂解的硫酯化和硒代酯化:从N-C(O)到S / Se-C(O)的相互转化

酰胺中直接亲核加成反应是有机合成中一种有吸引力的方法,该方法可通过基态失稳来解决酰胺共振。最近已经用碳,氮和氧亲核试剂完成了该方法。在本文中,我们报道了在不存在过渡金属的情况下通过选择性的N-C(O)键裂解直接进行酰胺的直接硫酯化和硒酯化的极其温和的方法。无环酰胺经过N-C(O)到S / Se-C(O)的相互转化,在室温下通过四面体中间途径(参见酰基金属)以优异的收率得到相应的硫酯和硒酸酯。
更新日期:2020-02-26
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