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利用硼氢化钠对一氧化碳进行还原甲酰化反应，实现芳香胺和脂肪胺的无催化剂甲酰化反应。

Catalyst free -formylation of aromatic and aliphatic amines exploiting reductive formylation of CO using NaBH.

作者信息

Kumar Arun, Sharma Pankaj, Sharma Nidhi, Kumar Yashwant, Mahajan Dinesh

机构信息

Medicinal Chemistry and Pharmacology Lab, Translational Health Science and Technology Institute (THSTI), NCR Biotech Science Cluster 3rd Milestone Faridabad-Gurgaon Expressway Faridabad-121001 India

出版信息

RSC Adv. 2021 Jul 27;11(41):25777-25787. doi: 10.1039/d1ra04848a. eCollection 2021 Jul 19.

DOI:10.1039/d1ra04848a
PMID:35478907
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9037105/
Abstract

Herein, we report a sustainable approach for -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 CO with sodium borohydride generates formoxy borohydride species , as confirmed by H and B NMR spectroscopy. The formation of formoxy borohydride species is prominent in formamide based solvents and is critical for the success of the -formylation reactions. The formoxy borohydride is also found to promote transamidation reactions as a competitive pathway along with reductive functionalization of CO with amine leading to -formylation of amines.

摘要

在此，我们报道了一种使用硼氢化钠和二氧化碳气体对芳香胺和脂肪胺进行α-甲酰化的可持续方法。所开发的方法无需催化剂，也不需要压力或专门的反应装置。通过氢和硼核磁共振光谱证实，硼氢化钠与一氧化碳的还原甲酰化反应生成甲酰氧基硼氢化物物种。甲酰氧基硼氢化物物种的形成在基于甲酰胺的溶剂中很显著，并且对于α-甲酰化反应的成功至关重要。还发现甲酰氧基硼氢化物会促进转酰胺反应，这是一条与一氧化碳与胺的还原官能化反应竞争的途径，后者会导致胺的α-甲酰化。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/1a0f99a0743c/d1ra04848a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/f94660ee9be6/d1ra04848a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/012716ca6406/d1ra04848a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/0a866f08db54/d1ra04848a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/e487f8bf5306/d1ra04848a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/2f13785d5ffe/d1ra04848a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/1a0f99a0743c/d1ra04848a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/f94660ee9be6/d1ra04848a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/012716ca6406/d1ra04848a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/0a866f08db54/d1ra04848a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/e487f8bf5306/d1ra04848a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/2f13785d5ffe/d1ra04848a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/81f3/9037105/1a0f99a0743c/d1ra04848a-f5.jpg

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