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草氨酸酯与芳基溴的氧化还原中性脱羧交叉偶联反应

Redox-Neutral Decarboxylative Cross-Coupling of Oxamates with Aryl Bromides.

作者信息

Bisoyi Akash, Simhadri Vijay Kumar, K Surya, Kuniyil Rositha, Yatham Veera Reddy

机构信息

School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram 695551, India.

Department of Chemistry, Indian Institute of Technology Palakkad, Kerala 678557, India.

出版信息

ACS Org Inorg Au. 2023 Nov 29;4(2):223-228. doi: 10.1021/acsorginorgau.3c00053. eCollection 2024 Apr 3.

Abstract

Dual nickel-photoredox-enabled direct synthesis of amides through cross-coupling of cesium oxamates with aryl bromides has been developed. This methodology's key advantages are mild reaction conditions, utilizing organic dye as a photocatalyst, employing readily available starting chemicals as coupling partners, and late-stage carbamoylation of pharmaceutically relevant molecules. DFT studies suggested that the nickel catalytic cycle proceeds via a radical addition pathway prior to the oxidative insertion.

摘要

已开发出通过草酸铯与芳基溴化物的交叉偶联实现双镍光氧化还原直接合成酰胺的方法。该方法的关键优势在于反应条件温和,使用有机染料作为光催化剂,采用易于获得的起始化学品作为偶联伙伴,以及对药物相关分子进行后期氨甲酰化。密度泛函理论研究表明,镍催化循环在氧化插入之前通过自由基加成途径进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b5/10996045/44d51fb8cf91/gg3c00053_0002.jpg

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