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镍催化的α-烯丙基溴代乙酰胺与芳基硼酸生成2-吡咯烷酮的环化/羰基化反应

Nickel-Catalyzed Cyclization/Carbonylation Reaction of -Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones.

作者信息

Ma Hucheng, Hou Chen-Yang, Zhao Ruyi, Qi Xinxin, Wu Xiao-Feng

机构信息

School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, People's Republic of China.

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023 Dalian, Liaoning, People's Republic of China.

出版信息

Org Lett. 2025 Feb 7;27(5):1299-1303. doi: 10.1021/acs.orglett.5c00003. Epub 2025 Jan 24.

Abstract

A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of -allylbromoacetamides toward the synthesis of 2-pyrrolidinone derivatives has been developed with arylboronic acids as the reaction partner. This transformation proceeds through a sequential single-electron-transfer pathway via 5-- cyclization and carbonyl insertion steps, furnishing a variety of 2-pyrrolidinone derivatives in good yields. Various useful functional groups were well tolerated. Moreover, formic acid is applied as the CO source here with nickel as the catalyst, which provides a good supplement for carbonylation chemistry and heterocycle synthesis.

摘要

已开发出一种直接有效的镍催化的烯丙基溴代乙酰胺环化/羰基化转化反应,以芳基硼酸作为反应伙伴来合成2-吡咯烷酮衍生物。该转化反应通过5-环化和羰基插入步骤的顺序单电子转移途径进行,以良好的产率提供了各种2-吡咯烷酮衍生物。各种有用的官能团都具有良好的耐受性。此外,在此以甲酸作为CO源,镍作为催化剂,这为羰基化化学和杂环合成提供了很好的补充。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e9bc/11812007/b9e097d6d3ff/ol5c00003_0001.jpg

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