A Photocatalytic Approach to Radical 1-(Trifluoromethyl)cyclopropanation

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-04-17 DOI:10.1021/acscatal.5c01642

Sven Timmann, Moritz T. H. Dilchert, Jörg Dietzel, Verena S. Pöltl, Marc R. Wennekamp, Christopher Golz, Manuel Alcarazo

引用次数: 0

Abstract

A simple protocol for the multigram-scale synthesis of 5-(1-(trifluoromethyl)cyclopropyl)dibenzothiophenium triflate is reported. This benchtop-stable reagent efficiently releases 1-(trifluoromethyl)cyclopropyl radicals under mild photochemical conditions, enabling the straightforward incorporation of that privileged chemotype at previously nonfunctionalized positions of (hetero)arenes and silyl enol ethers. The trifluoromethylcyclopropanation protocols herein reported are associated with an exceedingly broad substrate scope, remarkable functional group compatibility, high regioselectivity, and synthetically useful yields, making this reagent especially suitable for the preparation of medicinally relevant building blocks.

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1-（三氟甲基）自由基环丙烷化的光催化研究

报道了一种多克尺度合成5-（1-（三氟甲基）环丙基）二苯并噻吩三氟酸盐的简单方法。这种稳定的试剂在温和的光化学条件下有效地释放1-（三氟甲基）环丙基自由基，使得在（杂）芳烃和硅烯醚的先前非功能化位置上直接结合特权化学型。本文报道的三氟甲基环丙烷化方案具有非常广泛的底物范围、显著的官能团相容性、高区域选择性和合成有用的产率，使该试剂特别适合于制备医学相关的构建块。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.