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Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides.

ABSTRACT: The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.

SUBMITTER: Orduna JM

PROVIDER: S-EPMC9041104 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides.

Orduña Jose Maria JM Domínguez Gema G Pérez-Castells Javier J

RSC advances 20210913 48

The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into fl ...[more]

PMID: 35480268

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