9,10‐菲醌与Sn(OTf)2在氢原子转移途径下对醚直接曼尼希反应的协同光催化作用

IF 4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-10-04 DOI:10.1002/adsc.70101

Pradip Ramdas Thorve, Hun Young Kim, Kyungsoo Oh

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引用次数: 0

摘要

一个由9,10 -菲醌（o - PQ）和Sn(OTf)2组成的双光催化体系通过Csp3-H直接活化，实现了在可见光诱导下硝基酮的曼尼希型加成反应。这种不含氧化剂和还原剂的方法具有底物范围广、收率高、官能团耐受性好等特点。克尺度合成和下游转化（Suzuki, Sonogashira, Heck）证明了它的合成效用。机理研究表明，光激发的o - PQ - Sn（II）络合物介导氢原子转移，产生α -氧自由基，与Sn（II）活化的氮酮反应，形成协同循环。

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Cooperative Photocatalysis of 9,10‐Phenanthrenequinone and Sn(OTf)2 for Direct Mannich Reaction of Ethers via Hydrogen Atom Transfer Pathway

A dual photocatalytic system combining 9,10‐phenanthrenequinone (o‐PQ) and Sn(OTf)2 enabled the visible light‐induced Mannich‐type addition of ethers to nitrones via direct Csp3–H activation. This oxidant‐ and reductant‐free method featured broad substrate scope, good yields, and excellent functional group tolerance. Gram‐scale synthesis and downstream transformations (Suzuki, Sonogashira, Heck) demonstrated its synthetic utility. Mechanistic studies suggested a cooperative cycle where a photoexcited o‐PQ‐Sn(II) complex mediated hydrogen atom transfer, generating α‐oxy radicals that reacted with Sn(II)‐activated nitrones.

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来源期刊

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.