Gram-Scale Photocatalysis with a Stable and Recyclable Chromium(III) Photocatalyst in Acetonitrile and in Water

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-03-21 DOI:10.1002/adsc.202500075

Steven Sittel, Julian Neuner, Jonas M. Grenz, Christoph Förster, Robert Naumann, Katja Heinze

{"title":"Gram-Scale Photocatalysis with a Stable and Recyclable Chromium(III) Photocatalyst in Acetonitrile and in Water","authors":"Steven Sittel, Julian Neuner, Jonas M. Grenz, Christoph Förster, Robert Naumann, Katja Heinze","doi":"10.1002/adsc.202500075","DOIUrl":null,"url":null,"abstract":"The use of stable photosensitizers made on a multigram-scale from cheap and available starting materials offers an extraordinary opportunity to translate small-scale proof-of-concept photoreactions to widespread applications in non-specialized laboratories, thereby promoting the implementation of light-driven syntheses. Herein, we report an easy, multigram-scale preparation of the exceptionally photo- and redoxstable chromium(III) complex [Cr(tpe)2]3+ (tpe = 1,1,1-tris(pyrid-2-yl)ethane) at room temperature. This photocatalyst was successfully employed in acetonitrile and in the “green” solvent water as demonstrated in visible-light induced Schenck-Ene reactions, Newman-Kwart rearrangements, radical cation Diels-Alder cycloadditions, oxidative decarboxylation and trifluoromethylation reactions with excellent substrate conversions and high turnover numbers. Gram-scale photocatalytic reactions were conducted using a simple round-bottom flask as reaction vessel and irradiation with energy-efficient blue LEDs or even with sunlight. The stable photocatalyst was successfully recycled in up to 90–92 % yields after the photoreactions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"27 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202500075","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

Abstract

The use of stable photosensitizers made on a multigram-scale from cheap and available starting materials offers an extraordinary opportunity to translate small-scale proof-of-concept photoreactions to widespread applications in non-specialized laboratories, thereby promoting the implementation of light-driven syntheses. Herein, we report an easy, multigram-scale preparation of the exceptionally photo- and redoxstable chromium(III) complex [Cr(tpe)2]3+ (tpe = 1,1,1-tris(pyrid-2-yl)ethane) at room temperature. This photocatalyst was successfully employed in acetonitrile and in the “green” solvent water as demonstrated in visible-light induced Schenck-Ene reactions, Newman-Kwart rearrangements, radical cation Diels-Alder cycloadditions, oxidative decarboxylation and trifluoromethylation reactions with excellent substrate conversions and high turnover numbers. Gram-scale photocatalytic reactions were conducted using a simple round-bottom flask as reaction vessel and irradiation with energy-efficient blue LEDs or even with sunlight. The stable photocatalyst was successfully recycled in up to 90–92 % yields after the photoreactions.

查看原文本刊更多论文

求助全文

约1分钟内获得全文求助全文

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.