N-Heterocyclic Nitrenium-Catalyzed Photohomolysis of CF₃SO₂Cl for Alkene Trifluoromethylation

Organic Letters, Journal Year: 2023, Volume and Issue: 25(33), P. 6189 - 6194

Published: Aug. 14, 2023

N-Heterocyclic nitreniums (NHNs) have been utilized as Lewis acid catalysts to activate substrates with lone pairs. Alternative their conventional applications, we discovered that NHNs can also serve charge transfer complex catalysts. Herein, present another potential of by utilizing a weak interaction between and CF3SO2Cl. The method promotes CF3SO2Cl undergo photohomolysis, resulting in the CF3 radical. Mechanistic studies suggested could be due π-hole effect NHNs.

Language: Английский

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Radical Bifunctionalization of Alkenes with Arylsulfonylacetate as Bifunctional Reagent via Photoredox Radical Addition/Smiles Rearrangement Cascade

Published: Jan. 2, 2024

We present herein a modular photoredox strategy for the difunctionalization of alkenes employing arylsulfonyl acetate as bifunctional reagents. Under conditions, electrophilic carbon-centered radical, generated from reagent, add to followed by 1,4-aryltranlocation, providing robust alternative synthetic valuable γ,γ-diaryl and γ-aryl ester compounds. This method features mild reaction high atom- step- economy, excellent functional group compatibility great structural diversity. A complementary oxidative reagents activation mode governs radical cascade reactions, facilitating simultaneous incorporation aryl carboxylate bearing alkyl groups into alkenes.

Language: Английский

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Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/smiles rearrangement cascade

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110253 - 110253

Published: July 1, 2024

Language: Английский

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Lone Pair−π Interactions in Organic Reactions

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Noncovalent interactions between a lone pair of electrons and π systems can be categorized into two types based on the nature systems. Lone pair-π(C═O) with unsaturated, polarized bonds are primarily attributed to orbital interactions, whereas pair-π(Ar) aromatic functional groups result from electrostatic attractions (for electron-deficient aryls) or dispersion Pauli repulsions electron-rich/neutral aryls). Unlike well-established noncovalent pair-π have been comparatively underappreciated less used influence reaction outcomes. This review emphasizes experimental computational studies aimed at integrating design catalytic utilizing these regulate reactivity selectivity chemical transformations. The role is highlighted in stabilization destabilization transition states ground-state binding. Examples influenced by both rings as included. At variance previous reviews, present not structured according physical origin particular classes but divided chapters ways which affect kinetics and/or reactions.

Language: Английский

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Shining Light for Organophotocatalysed Site-selective Sulfonylation of Anilides

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(37), P. 7690 - 7695

Published: Jan. 1, 2024

An organophotocatalytic approach for the site-selective sulfonylation of C(sp 2 )–H bonds anilide and quinoline amide derivatives utilizing aryl sulfonyl chlorides as a sulfonylating agent is developed.

Language: Английский

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Paired Electrocatalysis-Enabled Cross Coupling of Sulfinamides with Olefins toward the Synthesis of Vinyl Sulfoximines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(40), P. 8463 - 8467

Published: Oct. 2, 2024

We present here a novel paired electrocatalysis-enabled convenient synthesis of the (

Language: Английский

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