Aerobic Allylation of Alcohols with Non-Activated Alkenes Enabled by Light-Driven Selenium-π-Acid Catalysis

Synthesis ◽  
2018 ◽  
Vol 50 (19) ◽  
pp. 3875-3885 ◽  
Author(s):  
Alexander Breder ◽  
Katharina Rode ◽  
Martina Palomba ◽  
Stefan Ortgies ◽  
Rene Rieger

A new organocatalytic protocol for the aerobic dehydrogenative allylation of alcohols using non-activated alkenes as the allylating reagent and ambient air as the terminal oxidant is established. Mechanistically, the procedure relies on the interplay of a diselane and a photo­redox catalyst by means of a light-induced electron transfer process. Under optimized conditions, a broad range of both cyclic and acyclic ethers is accessed with very high functional group tolerance and excellent regioselectivity.

Synlett ◽  
2018 ◽  
Vol 29 (04) ◽  
pp. 383-387 ◽  
Author(s):  
Wei Han ◽  
Binbin Liu

Compared with the widespread use of Pd-catalyzed Wacker-type oxidation of olefins, iron catalysis for this transformation is almost virgin territory. Our work on an iron-catalyzed Wacker-type oxidation through reductive activation of dioxygen is discussed here. This novel single-electron-transfer process not only addresses the issues of the Pd-catalyzed two-electron Wacker-type oxidation, but also possesses unprecedented functional-group tolerance and chemoselectivity. Importantly, the catalytic system uses ambient air as the sole oxidant, and it permits late-stage oxidations of complex molecules.


2016 ◽  
Vol 14 (48) ◽  
pp. 11415-11425 ◽  
Author(s):  
Gullapalli Kumaraswamy ◽  
Swargam Vijaykumar ◽  
Kukkadapu Ankamma ◽  
Vykunthapu Narayanarao

The stereoselective synthesis of α-phenylselenyl- or telluryl β-aryl acrylaldehydes/ketones from aryl allenes/1,3-diarylallene by an oxidative photo-induced single electron transfer process using benign ambient air as a sole oxidant was achieved.


2017 ◽  
Vol 19 (22) ◽  
pp. 14412-14423 ◽  
Author(s):  
Ewelina Krzyszkowska ◽  
Justyna Walkowiak-Kulikowska ◽  
Sven Stienen ◽  
Aleksandra Wojcik

Quenching of the thionine singlet excited state in covalently functionalized graphene oxide with an efficient back electron transfer process.


Nano Hybrids ◽  
2013 ◽  
Vol 3 ◽  
pp. 1-23 ◽  
Author(s):  
Chinwe O. Ikpo ◽  
Njagi Njomo ◽  
Kenneth I. Ozoemena ◽  
Tesfaye Waryo ◽  
Rasaq A. Olowu ◽  
...  

The electrochemical dynamics of a film of FeCo nanoparticles were studied on a glassy carbon electrode (GCE). The film was found to be electroactive in 1 M LiClO4 containing 1:1 v/v ethylene carbonate dimethyl carbonate electrolyte system. Cyclic voltammetric experiments revealed a diffusion-controlled electron transfer process on the GCE/FeCo electrode surface. Further interrogation on the electrochemical properties of the FeCo nanoelectrode in an oxygen saturated 1 M LiClO4 containing 1:1 v/v ethylene-carbonate-dimethyl carbonate revealed that the nanoelectrode showed good response towards the electro-catalytic reduction of molecular oxygen with a Tafel slope of about 120 mV which is close to the theoretical 118 mV for a single electron transfer process in the rate limiting step; and a transfer coefficient (α) of 0.49. The heterogeneous rate constant of electron transfer (ket), exchange current density (io) and time constant (τ) were calculated from data obtained from electrochemical impedance spectroscopy and found to have values of 2.3 x 10-5 cm s-1, 1.6 x 10-4 A cm-2 and 2.4 x 10-4 s rad-1, respectively.


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