Proton-Coupled Electron Transfer and Substituent Effects in Catechol-Based Deep Eutectic Solvents: Gross and Fine Tuning of Redox Activity

Parker J. Smith; John C. Goeltz

doi:10.1021/acs.jpcb.7b10169

Proton-Coupled Electron Transfer and Substituent Effects in Catechol-Based Deep Eutectic Solvents: Gross and Fine Tuning of Redox Activity

The Journal of Physical Chemistry B ◽

10.1021/acs.jpcb.7b10169 ◽

2017 ◽

Vol 121 (48) ◽

pp. 10974-10978 ◽

Cited By ~ 2

Author(s):

Parker J. Smith ◽

John C. Goeltz

Keyword(s):

Electron Transfer ◽

Substituent Effects ◽

Deep Eutectic Solvents ◽

Fine Tuning ◽

Redox Activity ◽

Proton Coupled Electron Transfer

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Guanidines as Reagents in Proton-Coupled Electron-Transfer Reactions and Redox Catalysts

Synlett ◽

10.1055/s-0037-1610156 ◽

2018 ◽

Vol 29 (15) ◽

pp. 1957-1977 ◽

Cited By ~ 15

Author(s):

Hans-Jörg Himmel

Keyword(s):

Electron Transfer ◽

Transfer Reactions ◽

Redox Activity ◽

Coupling Reactions ◽

Proton Coupled Electron Transfer ◽

Redox Catalysts ◽

Dehydrogenative Coupling ◽

Redox Active ◽

Organic Electron ◽

Donor Acceptor

Redox-active guanidines are ideal proton-coupled electron-transfer (PCET) reagents, since they combine a high Brønsted basicity with a low and tunable redox potential. In this article, the development of redox-active guanidines (especially guanidino-functionalized aromatics, GFAs) in the last ten years is summarized, and their properties compared to other organic Brønsted bases and organic electron donors. First, some applications in organic chemistry that purely use the redox activity (formation of organic donor–acceptor materials and photochemical reductive C–C coupling reactions) are presented. Then, reactions that involve both proton and electron transfer are reviewed. In stoichiometric reactions, redox-active guanidines are used for the dehydrogenative coupling of thiols and phosphanes. The first redox catalytic applications are discussed, using dioxygen as green oxidizing reagent.1 Introduction2 Redox-Active Amines and Guanidines3 Brønsted Basicity of Amines and Guanidines4 Variations of GFA Compounds5 GFA Compounds in Organic Donor–Acceptor Materials and as Reducing Reagents in Organic Synthesis6 Stoichiometric Dehydrogenative Coupling Reactions with Redox-Active Guanidines7 Guanidines as Redox Catalysts8 Conclusions and Outlook

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A Titanium(III) Phosphite Exhibits Polymorph-Distinct Redox Activity Involving Proton-Coupled Electron Transfer

Chemical Communications ◽

10.1039/d1cc01190a ◽

2021 ◽

Author(s):

Ling-I Hung ◽

Tsung-Hsiu Hsieh ◽

Jhao-Yang Syu ◽

Pei-Lin Chen ◽

Chia-Her Lin ◽

...

Keyword(s):

Electron Transfer ◽

Solid State ◽

Redox Activity ◽

Proton Distribution ◽

Proton Coupled Electron Transfer

A novel titanium(III) phosphite with intriguing polymorphism and solid-state proton-coupled electron transfer (PCET) oxidation is presented. The polymorphs show structure-dependent PCET reactivity, interpretable by proton distribution in channels. Combined with...

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