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光氧化还原催化下三氟乙酸酐对(杂)芳基和极性烯烃的三氟甲基化反应。

Trifluoromethylations of (Hetero)arenes and Polarized Alkenes Using Trifluoroacetic Anhydride under Photoredox Catalysis.

机构信息

Jilin Province Key Laboratory of Organic Functional Molecular, Design & Synthesis, Department of Chemistry, Northeast Normal University, 5268 Renmin Street, Changchun 130024, China.

出版信息

Org Lett. 2023 Apr 7;25(13):2372-2376. doi: 10.1021/acs.orglett.3c00890. Epub 2023 Mar 27.

DOI:10.1021/acs.orglett.3c00890
PMID:36971301
Abstract

A novel trifluoromethylation of (hetero)arenes and polarized alkenes using simple trifluoroacetic anhydride (TFAA) as the low price CF source under photoredox catalysis was developed without using additives such as bases, hyperstoichiometric oxidant, or auxiliaries. The reaction showed excellent tolerance, including to some important natural products and prodrugs, even on the gram scale and extended to ketones. This simple protocol provides a practical utilization of TFAA. Several perfluoroalkylations and trifluoromethylation/cyclizations were successfully achieved under identical conditions.

摘要

在光氧化还原催化作用下,使用廉价的三氟乙酸酐(TFAA)作为 CF 源,开发了一种新型(杂)芳基和极性烯烃的三氟甲基化方法,无需使用碱、过化学计量的氧化剂或助剂等添加剂。该反应具有出色的耐受性,包括对一些重要的天然产物和前药,甚至在克级规模上也能进行,并扩展到酮类。该简单方案为 TFAA 的实际应用提供了一种可能。在相同条件下,成功实现了几种全氟烷基化和三氟甲基化/环化反应。

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