A General Red‐Light Photocatalytic Platform for the Synthesis of Perfluoroalkyl Tellanes

IF 3.7 2区 化学 Q2 CHEMISTRY, APPLIED
Sheila G. Perez Edighill, Damian E. Yerien, Sebastian Barata‐Vallejo, Al Postigo
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引用次数: 0

Abstract

Perfluoroalkyl tellanes (R F –Te–R) constitute a synthetically valuable yet underdeveloped class of organotellurium compounds, despite their potential in fluoroorganic chemistry and materials science. Herein, we disclose a general, efficient, and operationally simple photocatalytic strategy for their synthesis from readily available ditellanes and perfluoroalkyl iodides. The transformation is enabled by red‐light irradiation in the presence of zinc phthalocyanine as an inexpensive and readily accessible photocatalyst, allowing the generation of perfluoroalkyl radicals under exceptionally mild conditions. This protocol exhibits broad substrate scope, accommodating a wide range of diaryl, heteroaryl, and dialkyl ditellanes, including sterically congested and biologically relevant scaffolds, and consistently delivers the corresponding perfluoroalkyl tellanes in high yields. Mechanistic studies, including radical trapping experiments, Stern–Volmer analysis, and quantum yield determination ( Φ = 2.4), reveal a photoinitiated radical chain mechanism in which the inherent lability of the Te─Te bond plays a key role in facilitating efficient radical capture and propagation. By combining low‐energy photochemical activation with the unique reactivity of tellurium‐centered species, this work establishes a practical and scalable platform for C─Te bond formation and significantly expands the synthetic toolbox for accessing perfluoroalkyl tellanes.
合成全氟烷基碲烷的通用红光光催化平台
全氟烷基tellanes (R F -Te-R)是一类具有合成价值但尚未开发的有机碲化合物,尽管它们在氟有机化学和材料科学中具有潜力。在此,我们公开了一种通用的、高效的、操作简单的光催化策略,用于从现成的二苯醚和全氟烷基碘化物合成它们。这种转化是在酞菁锌存在的红光照射下实现的,酞菁锌是一种廉价且容易获得的光催化剂,允许在非常温和的条件下生成全氟烷基自由基。该方案具有广泛的底物范围,可容纳广泛的二芳基、杂芳基和二烷基二碲烷,包括空间拥塞和生物相关的支架,并始终如一地以高产量提供相应的全氟烷基碲烷。机理研究,包括自由基捕获实验,Stern-Volmer分析和量子产率测定(Φ = 2.4),揭示了光引发自由基链机制,其中Te─Te键的固有不稳定性在促进有效的自由基捕获和传播中起着关键作用。通过将低能光化学活化与碲中心物质的独特反应活性相结合,本研究建立了一个实用且可扩展的C─Te键形成平台,并显著扩展了获取全氟烷基碲烷的合成工具箱。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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