ArticleACS central science2017
Lewis Acid Induced Toggle from Ir(II) to Ir(IV) Pathways in Photocatalytic Reactions: Synthesis of Thiomorpholines and Thiazepanes from Aldehydes and SLAP Reagents.
Article in ACS central science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 43 citations in OpenAlex.
- Copper-Catalyzed Three-Component Synthesis of Highly Substituted Morpholines.Organic letters · 2024Article
- Investigations into mechanism and origin of regioselectivity in the metallaphotoredox-catalyzed α-arylation ofChemical science · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Modular synthesis and transition metal-free alkynylation/alkenylation of Castagnoli-Cushman-derivedRSC advances · 2020Article
- Catalytic C(spNature chemistry · 2020Article
- Expedient access to saturated nitrogen heterocycles by photoredox cyclization of imino-tethered dihydropyridines.Chemical science · 2019Article
- Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles.Organic letters · 2019Article
- Enabling synthesis in fragment-based drug discovery by reactivity mapping: photoredox-mediated cross-dehydrogenative heteroarylation of cyclic amines.Chemical science · 2019Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Redox neutral photocatalytic transformations often require careful pairing of the substrates and photoredox catalysts in order to achieve a catalytic cycle. This can limit the range of viable transformations, as we recently observed in attempting to extend the scope of the photocatalytic synthesis of N-heterocycles using silicon amine protocol (SLAP) reagents to include starting materials that require higher oxidation potentials. We now report that the inclusion of Lewis acids in photocatalytic reactions of organosilanes allows access to a distinct reaction pathway featuring an Ir(III)*/Ir(IV) couple instead of the previously employed Ir(III)*/Ir(II) pathway, enabling the transformation of aromatic and aliphatic aldehydes to thiomorpholines and thiazepanes. The role of the Lewis acid in accepting an electron-either directly or via coordination to an imine-can be extended to other classes of photocatalysts and transformations, including oxidative cyclizations. The combination of light induced reactions and Lewis acids therefore promises access to new pathways and transformations that are not viable using the photocatalysts alone.
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Registered trials
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