ArticleThe Journal of organic chemistry2018
Photoredox Cyanomethylation of Indoles: Catalyst Modification and Mechanism.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Article
- Carbon Dots as Nano-Photocatalysts: A Green Tool for Indole and Heteroarenes Alkylation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- High-Throughput Determination of Stern-Volmer Quenching Constants for Common Photocatalysts and Quenchers.ACS organic & inorganic Au · 2023Article
- Efforts toward Synthetic Photosynthesis: Visible Light-Driven COJournal of the American Chemical Society · 2023Article
- Regioselective Radical Alkylation of Arenes Using Evolved Photoenzymes.Journal of the American Chemical Society · 2023Article
- Visible-Light-Promoted Direct C3-H Cyanomethylation of 2ACS omega · 2023Article
- Regioselective Radical Alkylation of Arenes Using Evolved Photoenzymes.Research square · 2023Article
- Ni single atoms on carbon nitride for visible-light-promoted full heterogeneous dual catalysis.Chemical science · 2022Article
- A computational study for the reaction mechanism of metal-free cyanomethylation of aryl alkynoates with acetonitrile.RSC advances · 2021Article
- Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation.Communications chemistry · 2021Article
- Selectivity in the Addition of Electron Deficient Radicals to theEuropean journal of organic chemistry · 2020Article
- Photocatalytic Synthesis of Polycyclic Indolones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Radical cyanomethylationChemical science · 2019Article
- Application of Plasma Treatment in Preparation of Soybean Oil Factory Sludge Catalyst and Its Application in Selective Catalytic Oxidation (SCO) Denitration.Materials (Basel, Switzerland) · 2018Article
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Authors and funding
7 authors.
Funding
Abstract
The direct cyanomethylation of indoles at the 2- or 3-position was achieved via photoredox catalysis. The versatile nitrile synthon is introduced as a radical generated from bromoacetonitrile, a photocatalyst, and blue LED as a light source. The mechanism of the reaction is explored by determination of the Stern-Volmer quenching constants. By combining photophysical data and mass spectrometry to follow the catalyst decomposition, the catalyst ligands were tuned to enable synthetically useful yields of radical coupling products. A range of indole substrates with alkyl, aryl, halogen, ester, and ether functional groups participate in the reaction, affording products in 16-90% yields. The reaction allows the rapid construction of synthetically useful cyanomethylindoles, products that otherwise require several synthetic steps.
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