Photoredox-Catalyzed Markovnikov Hydroamination of Alkenes with Azoles

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-30 DOI:10.1021/acs.orglett.4c0341810.1021/acs.orglett.4c03418

Jinhuan Nie, Yutao Shi, Mengran Gan, Huawen Huang and Xiaochen Ji*,

引用次数: 0

Abstract

A visible-light induced intermolecular hydroamination of alkenes with azoles is reported, delivering pharmaceutically valuable N-benzyl azoles in high yields with excellent Markovnikov selectivity. Mechanistic studies suggest that the process is initiated by the energy transfer of the excited photocatalyst with alkenes, followed by the single electron reduction, protonation, and subsequent single electron oxidation to afford the key alkyl carbocation intermediate. This protocol exhibits advantages of broad functional group tolerance, excellent atom economy, high efficiency, and mild reaction conditions.

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光氧化催化烯与唑的马尔科夫尼科夫氢化反应

据报道，一种可见光诱导的烯与唑的分子间氢化反应，能以高产率和出色的马尔科夫尼科夫选择性提供具有药用价值的 N-苄基唑。机理研究表明，该过程是由受激光催化剂与烯烃的能量转移启动的，随后是单电子还原、质子化和随后的单电子氧化，从而产生关键的烷基碳化中间体。该方案具有广泛的官能团耐受性、出色的原子经济性、高效率和反应条件温和等优点。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.