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Catalyst free N-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO₂ using NaBH₄.

ABSTRACT: Herein, we report a sustainable approach for N-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO₂ with sodium borohydride generates formoxy borohydride species in situ, as confirmed by ¹H and ¹¹B NMR spectroscopy. The in situ formation of formoxy borohydride species is prominent in formamide based solvents and is critical for the success of the N-formylation reactions. The formoxy borohydride is also found to promote transamidation reactions as a competitive pathway along with reductive functionalization of CO₂ with amine leading to N-formylation of amines.

SUBMITTER: Kumar A

PROVIDER: S-EPMC9037105 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Catalyst free N-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO2 using NaBH4.

Kumar Arun A Sharma Pankaj P Sharma Nidhi N Kumar Yashwant Y Mahajan Dinesh D

RSC advances 20210727 41

Herein, we report a sustainable approach for N-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO2 with sodium borohydride generates formoxy borohydride species in situ, as confirmed by 1H and 11B NMR spectroscopy. The in situ formation of formoxy borohydride ...[more]

PMID: 35478907

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