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有机光氧化还原催化实现的三氟甲基烯烃与叠氮基三甲基硅烷的氢叠氮化反应。

Hydroazidation of trifluoromethyl alkenes with trimethylsilyl azide enabled by organic photoredox catalysis.

作者信息

Shi Yutao, Zhang Yuliang, Ji Xiaochen, Huang Huawen

机构信息

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, China.

出版信息

Chem Commun (Camb). 2024 Jul 23;60(60):7741-7744. doi: 10.1039/d4cc02503b.

Abstract

Herein, we report an organic photoredox-catalyzed hydroazidation of trifluoromethyl alkenes with user-friendly trimethylsilyl azide (TMSN), enabling a direct access to a broad range of valuable β-CF-azides with exclusive selectivity under mild reaction conditions. The synthetic utility of this reaction was demonstrated by the late-stage modification of complex drug derivatives, scale-up of the reaction and diverse further derivatizations of the β-CF-azide product.

摘要

在此,我们报道了一种有机光氧化还原催化的三氟甲基烯烃与使用方便的叠氮基三甲基硅烷(TMSN)的氢叠氮化反应,该反应能够在温和的反应条件下以独特的选择性直接获得多种有价值的β-CF-叠氮化物。该反应的合成实用性通过复杂药物衍生物的后期修饰、反应放大以及β-CF-叠氮化物产物的多种进一步衍生化得以证明。

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