Spectroscopic Determination of Proton Position in the Proton-Coupled Electron Transfer Pathways of Donor−Acceptor Supramolecule Assemblies

2006 ◽  
Vol 128 (32) ◽  
pp. 10474-10483 ◽  
Author(s):  
Joel Rosenthal ◽  
Justin M. Hodgkiss ◽  
Elizabeth R. Young ◽  
Daniel G. Nocera
Keyword(s):  
Electron Transfer ◽  
Spectroscopic Determination ◽  
Proton Coupled Electron Transfer ◽  
Donor Acceptor ◽  
Electron Transfer Pathways

Switching between Stepwise and Concerted Proton-Coupled Electron Transfer Pathways in Tungsten Hydride Activation

2018 ◽  
Vol 140 (44) ◽  
pp. 14655-14669 ◽  
Author(s):  
Tao Huang ◽  
Eric S. Rountree ◽  
Andrew P. Traywick ◽  
Magd Bayoumi ◽  
Jillian L. Dempsey
Keyword(s):  
Electron Transfer ◽  
Proton Coupled Electron Transfer ◽  
Electron Transfer Pathways

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

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 1957-1977 ◽  
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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