Transfer learning across different photocatalytic organic reactions

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 10, 2025

Language: Английский

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Expanding the Use of Benzothioxanthene Imides to Photochemistry: Eco‐Friendly Aerobic Oxidation of Sulfides to Sulfoxides

ChemSusChem, Journal Year: 2024, Volume and Issue: unknown

Published: June 13, 2024

The sulfoxide moiety is one of the most commonly utilized groups in pharmaceutical and industrial chemistry. need for sustainability easy accessibility to moieties deemed necessary, due its ubiquity natural products potentially pharmaceutically active compounds. In this context, we report herein a sustainable, aerobic environmentally friendly photochemical protocol based on use benzothioxathene imide as photocatalyst selectively oxidize sulfides under mild irradiation (456 nm), very low catalyst loading (0.01 mol %) water. addition, demonstrate compatibility our with wide scope substrates, latter was successfully applied synthesis biologically-active Sulforaphane Modafinil.

Language: Английский

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Cyclic Bifunctional Reagents Enabling a Strain-Release-Driven Formal [3 + 2] Cycloaddition of 2H-Azirines by Cascade Energy Transfer

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 10, 2025

The energy transfer (EnT)-catalyzed ring opening and further decarboxylation of isoxazole-5(4H)-ones enables the in situ generation strained 2H-azirines. Subsequent selective C(sp2)-C(sp3) bond cleavage azirine intermediate allows a formal [3 + 2] cycloaddition with wide range electrophiles, unlocking access to valuable pyrroline-type moieties. Mechanistic experiments combination density functional theory (DFT) calculations revealed unique nature EnT-cascade process for three-membered aza-cycle while providing insight into regio- diastereoselectivity annulation. This mild straightforward method ensures rapid construction highly substituted cyclic imines, which can be easily converted pyrrolidines, fused oxaziridines, biologically relevant β-amino acid precursors.

Language: Английский

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Controllable Radical Reactions of 1,3-Dienes with Light

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7749 - 7779

Published: April 25, 2025

Language: Английский

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Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters

Beilstein Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 21, P. 854 - 863

Published: April 30, 2025

The photoactivation of organic molecules via energy transfer (EnT) catalysis is often limited to conjugated systems that have low-energy triplet excited states, with simple alkenes remaining an intractable challenge. ability address this limitation, using high sensitizers, would represent attractive platform for future reaction design. Here, we disclose the alkenylboronic esters established alkene scrambling as a rapid probe identify suitable catalyst and boron motif. Cyclic voltammetry, UV–vis analysis, control reactions support sensitization, enabling intramolecular [2 + 2] cycloaddition be realized accessing 3D bicyclic fragments containing handle.

Language: Английский

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Combined machine learning and computational protocols to predict electrolyte behavior and SEI formation in Li-metal batteries

Chemical Engineering Journal, Journal Year: 2025, Volume and Issue: unknown, P. 163801 - 163801

Published: May 1, 2025

Language: Английский

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Regioselectivity of non-Symmetrical Borylated Dienes via EnT Ca-talysis: Unveiling the Relationship between Structure and Reactivity

Published: Aug. 16, 2024

Energy transfer catalysis (EnT) has had a profound impact on contemporary organic synthesis enabling the construction of higher in energy, complex molecules, via efficient access to triplet excited state. Despite this, intermolecular reactivity, and unique possibility several reaction pathways central diradical rendered control over outcomes, an intractable challenge. Extended chromophores such as non-symmetrical dienes have potential undergo 2+2 cycloaddition, 4+2 cycloaddition or geometric isomerization, which, combination with other mechanistic considerations (site- regioselectivity), results chemical reactions that are challenging regulate. Leveraging spin density predictive tool, use core functionality can be adequately tuned potentially modulate would highly revealing intimate links between structure EnT induced reactivity. Herein, we utilize boron tool explore reactivity under catalysis, paying particular attention hybridization effects target Through site- regioselective was realized employed motif effecting efficiency. Reaction divergence enable achieved, while counterintuitive regiodivergence observed isomerization versus cycloaddition. The validated in-depth investigation determining origin competing processes

Language: Английский

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1,1′-Diarylethylene as a Key Additive for the Visible Light Synthesis of Bioactive Dihydrobenzo[a]phenanthridine Compounds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(20), P. 15117 - 15136

Published: Oct. 1, 2024

This study introduces a straightforward synthetic approach for generating 7,8-dihydrobenzo[

Language: Английский

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Formal Transformation of Benzylic Carboxylic Acids to Phenols

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 14, 2024

Abstract Phenols play a crucial role as core structural motifs in natural products and also serve fundamental building blocks synthetic chemistry. Apart from the known protocols for conversion of aryl precursors to phenols (i. e., decarboxylative oxygenation), we report here efficient synthesis stable readily available benzylic carboxylic acids under mild reaction conditions. The photocatalytic peroxides is step this strategy, allowing subsequent C−O bond formation via Hock rearrangement.

Language: Английский

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