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Relevant academic research and scientific papers

A Novel Thermomorphic System for Electrocatalytic Diels-Alder Reactions

The discovery that lithium bis(trifluoromethane)sulfonamide (LiTFSI)/1-nitropropane (PrNO2) solution functions as a less polar alternative to lithium perchlorate (LiClO4)/nitromethane (MeNO2) solution has led to the develo

Investigating radical cation chain processes in the electrocatalytic Diels-Alder reaction

Single electron transfer (SET)-triggered radical ion-based reactions have proven to be powerful options in synthetic organic chemistry. Although unique chain processes have been proposed in various photo- and electrochemical radical ion-based transformati

Mechanistic Insights on Concentrated Lithium Salt/Nitroalkane Electrolyte Based on Analogy with Fluorinated Alcohols

Fluorinated alcohols such as 1,1,1,3,3,3-hexafluoro2-propanol (HFIP) and 2,2,2-trifluoroethanol (TFE) have emerged as powerful solvents in oxidation chemistry including hole catalysis. In this paper, we describe the similarity of lithium salt/nitroalkane

Discovery and Elucidation of Counteranion Dependence in Photoredox Catalysis

Over the past decade, there has been a renewed interest in the use of transition metal polypyridyl complexes as photoredox catalysts for a variety of innovative synthetic applications. Many derivatives of these complexes are known, and the effect of ligand modifications on their efficacy as photoredox catalysts has been the subject of extensive, systematic investigation. However, the influence of the photocatalyst counteranion has received little attention, despite the fact that these complexes are generally cationic in nature. Herein, we demonstrate that counteranion effects exert a surprising, dramatic impact on the rate of a representative photocatalytic radical cation Diels-Alder reaction. A detailed analysis reveals that counteranion identity impacts multiple aspects of the reaction mechanism. Most notably, photocatalysts with more noncoordinating counteranions yield a more powerful triplet excited state oxidant and longer radical cation chain length. It is proposed that this counteranion effect arises from Coulombic ion-pairing interactions between the counteranion and both the cationic photoredox catalyst and the radical cation intermediate, respectively. The comparatively slower rate of reaction with coordinating counteranions can be rescued by using hydrogen-bonding anion binders that attenuate deleterious ion-pairing interactions. These results demonstrate the importance of counteranion identity as a variable in the design and optimization of photoredox transformations and suggest a novel strategy for the optimization of organic reactions using this class of transition metal photocatalysts.

Visible-Light-Irradiated Graphitic Carbon Nitride Photocatalyzed Diels–Alder Reactions with Dioxygen as Sustainable Mediator for Photoinduced Electrons

Photocatalytic Diels–Alder (D–A) reactions with electron rich olefins are realized by graphitic carbon nitride (g-C3N4) under visible-light irradiation and aerobic conditions. This heterogeneous photoredox reaction system is highly e

Host-Guest-Induced Electron Transfer Triggers Radical-Cation Catalysis

Modifying the reactivity of substrates by encapsulation is a fundamental principle of capsule catalysis. Here we show an alternative strategy, wherein catalytic activation of otherwise inactive quinone "co-factors" by a simple Pd2L4 capsule promotes a range of bulk-phase, radical-cation cycloadditions. Solution electron-transfer experiments and cyclic voltammetry show that the cage anodically shifts the redox potential of the encapsulated quinone by a significant 1 V. Moreover, the capsule also protects the reduced semiquinone from protonation, thus transforming the role of quinones from stoichiometric oxidants into catalytic single-electron acceptors. We envisage that the host-guest-induced release of an "electron hole" will translate to various forms of non-encapsulated catalysis that involve other difficult-to-handle, highly reactive species.

Entropic electrolytes for anodic cycloadditions of unactivated alkene nucleophiles

Unactivated alkenes were previously found to be effective carbon nucleophiles for anodic cycloadditions in lithium perchlorate/nitromethane electrolyte solution. Herein,7Li NMR analysis and calorimetric studies clearly illustrate that the entro

Detection of transient radical cations in electron transfer-initiated Diels-Alder reactions by electrospray ionization mass spectrometry

The coupling of a simple microreactor to an atmospheric pressure ion source, such as electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI), allows the investigation of reactions in solution by mass spectrometry. The tris(p-bromo

Photocatalytic Cycloadditions Enabled by a Lithium Perchlorate/Nitromethane Electrolyte Solution

Photocatalytic cycloadditions involving carbon–carbon bond formation in the absence of an external sensitizer are described. The use of a lithium perchlorate/nitromethane electrolyte solution exhibiting remarkable Lewis acidity is the key for the successf

Benign catalysis with iron: Facile assembly of cyclobutanes and cyclohexenes: Via intermolecular radical cation cycloadditions

We describe novel and facile iron-catalyzed crossed intermolecular radical cation cycloadditions of styrenes. This catalysis features high efficiency, atom economy, stereospecificity, scalability and very mild reaction conditions. Thus, these reactions re