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无介质电化学三氟甲基化:一种合成三氟甲基异恶唑啉的串联方法。

Mediator-free electrochemical trifluoromethylation: a cascade approach for the synthesis of trifluoromethylated isoxazolines.

作者信息

Mahanty Kingshuk, Saha Suman Kumar, Halder Atreyee, De Sarkar Suman

机构信息

Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur-741246, West Bengal, India.

出版信息

Chem Commun (Camb). 2023 Apr 11;59(30):4467-4470. doi: 10.1039/d3cc00231d.

Abstract

The developed methodology describes an environmentally benign protocol for electro-oxidative CF-radical generation, followed by cascade cyclization fabricating an isoxazoline scaffold from a β,γ-unsaturated oxime. Consecutive C-O and C-C bond formations were achieved through this method featuring mild, robust, and scalable reaction conditions and broad substrate scope. Mechanistic studies revealed the necessity of anodic oxidation for the cascade process. Further conversion of the isoxazoline afforded other valuable derivatives.

摘要

所开发的方法描述了一种环境友好的电氧化CF-自由基生成方案,随后通过级联环化从β,γ-不饱和肟制备异恶唑啉支架。通过该方法实现了连续的C-O和C-C键形成,该方法具有温和、稳健且可扩展的反应条件以及广泛的底物范围。机理研究揭示了级联过程中阳极氧化的必要性。异恶唑啉的进一步转化得到了其他有价值的衍生物。

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