Catalytic photoactivation of a triarylamine electron donor-acceptor complex for difunctionalization of alkenes

IF 7.9 2区 综合性期刊 Q1 CHEMISTRY, MULTIDISCIPLINARY Cell Reports Physical Science Pub Date : 2024-08-02 DOI:10.1016/j.xcrp.2024.102135
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Abstract

The photoactivation of electron donor-acceptor complexes is a useful tool for the generation of radical species in synthetic chemistry. However, alkene difunctionalization via catalytic donor-acceptor complexes remains less developed. Herein, we report a versatile catalytic photoactivation of an electron donor-acceptor complex platform for the difunctionalization of alkenes without a need for precious transition metal catalysts or synthetically elaborate organic dyes. By taking advantage of the visible light potential of aggregates between triarylamines and S-fluoromethyldiaryl sulfonium salts, photoinduced single-electron transfer is initiated to generate a stable radical cation, which acts as an endogenous oxidant to convert the radical addition intermediate into a cationic species. Subsequent N-nucleophilic addition enables the difunctionalization of styrenes. This general photocatalyst-free protocol is applied to fluoroalkylative sulfonamidation, amidation, hydrazidation, azidation, and anilination reactions under mild conditions.

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催化光活化三芳基胺电子供体-受体复合物实现烯烃的双官能化
电子供体-受体复合物的光活化是合成化学中生成自由基物种的有用工具。然而,通过催化供体-受体复合物进行烯烃双官能化的研究仍然较少。在此,我们报告了一种电子供体-受体复合物平台的多功能催化光活化技术,该技术可用于烯烃的双官能化,而无需贵重的过渡金属催化剂或合成精细的有机染料。利用三芳基胺和 S-氟甲基二芳基锍盐之间的聚合体的可见光电位,光诱导单电子转移开始生成稳定的自由基阳离子,该阳离子作为内源氧化剂将自由基加成中间体转化为阳离子物种。随后的 N-亲核加成可实现苯乙烯的反官能化。在温和的条件下,这种通用的无光催化剂方案可用于氟烷基磺酰胺化、酰胺化、肼化、叠氮化和苯胺化反应。
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来源期刊
Cell Reports Physical Science
Cell Reports Physical Science Energy-Energy (all)
CiteScore
11.40
自引率
2.20%
发文量
388
审稿时长
62 days
期刊介绍: Cell Reports Physical Science, a premium open-access journal from Cell Press, features high-quality, cutting-edge research spanning the physical sciences. It serves as an open forum fostering collaboration among physical scientists while championing open science principles. Published works must signify significant advancements in fundamental insight or technological applications within fields such as chemistry, physics, materials science, energy science, engineering, and related interdisciplinary studies. In addition to longer articles, the journal considers impactful short-form reports and short reviews covering recent literature in emerging fields. Continually adapting to the evolving open science landscape, the journal reviews its policies to align with community consensus and best practices.
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