scholarly journals Time-Resolved Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light

Author(s):  
Rajdip Chowdhury ◽  
Zhunzhun Yu ◽  
Stefanie V. Kohlhepp ◽  
Xiang Yin ◽  
Abraham Mendoza

<div><div><div><p>Flexible, small and strong alkyl ligations created upon external light stimuli can open new avenues for medicinal and biological research. Herein, we have found that NADH and analogues can drive photo-couplings without auxiliary photocatalysts. The time- resolved alkyl photo-ligation between redox-active carboxylate derivatives and electron-poor olefins displays a surprising moisture and air-tolerance, and unusually high coupling rates in dilute conditions. This work sets the conceptual basis for further biocompatible C-C coupling reactions promoted by visible-light in combination with NADH, the ubiquitous reductant of biological systems.</p></div></div></div>

2020 ◽  
Author(s):  
Rajdip Chowdhury ◽  
Zhunzhun Yu ◽  
Stefanie V. Kohlhepp ◽  
Xiang Yin ◽  
Abraham Mendoza

<div><div><div><p>Flexible, small and strong alkyl ligations created upon external light stimuli can open new avenues for medicinal and biological research. Herein, we have found that NADH and analogues can drive photo-couplings without auxiliary photocatalysts. The time- resolved alkyl photo-ligation between redox-active carboxylate derivatives and electron-poor olefins displays a surprising moisture and air-tolerance, and unusually high coupling rates in dilute conditions. This work sets the conceptual basis for further biocompatible C-C coupling reactions promoted by visible-light in combination with NADH, the ubiquitous reductant of biological systems.</p></div></div></div>


Author(s):  
Jia-Xin Wang ◽  
Ya-Ting Wang ◽  
Hao Zhang ◽  
Ming-Chen Fu

A visible-light-induced iodine anion catalyzed C-H stereoselective alkylation of enamides has been developed. Redox-active esters and Katritzky salts of the amino acid are amenable for decarboxylative/deaminative cross-coupling reactions, delivering various...


2015 ◽  
Vol 11 ◽  
pp. 930-948 ◽  
Author(s):  
Huixin Jiang ◽  
Virginia Mazzanti ◽  
Christian R Parker ◽  
Søren Lindbæk Broman ◽  
Jens Heide Wallberg ◽  
...  

A selection of cyclic and acyclic acetylenic scaffolds bearing two tetrathiafulvalene (TTF) units was prepared by different metal-catalyzed coupling reactions. The bridge separating the two TTF units was systematically changed from linearly conjugated ethyne, butadiyne and tetraethynylethene (trans-substituted) units to a cross-conjugated tetraethynylethene unit, placed in either acyclic or cyclic arrangements. The cyclic structures correspond to so-called radiaannulenes having both endo- and exocyclic double bonds. Interactions between two redox-active TTF units in these molecules were investigated by cyclic voltammetry, UV–vis–NIR and EPR absorption spectroscopical methods of the electrochemically generated oxidized species. The electron-accepting properties of the acetylenic cores were also investigated electrochemically.


2008 ◽  
Vol 163 (4-6) ◽  
pp. 545-550
Author(s):  
G. Privitera ◽  
L. Lanzanò ◽  
A. Scordino ◽  
S. Tudisco ◽  
F. Musumeci ◽  
...  

Science ◽  
2019 ◽  
Vol 364 (6439) ◽  
pp. eaav9713 ◽  
Author(s):  
Asik Hossain ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser

Visible-light photoredox catalysis offers a distinct activation mode complementary to thermal transition metal catalyzed reactions. The vast majority of photoredox processes capitalizes on precious metal ruthenium(II) or iridium(III) complexes that serve as single-electron reductants or oxidants in their photoexcited states. As a low-cost alternative, organic dyes are also frequently used but in general suffer from lower photostability. Copper-based photocatalysts are rapidly emerging, offering not only economic and ecological advantages but also otherwise inaccessible inner-sphere mechanisms, which have been successfully applied to challenging transformations. Moreover, the combination of conventional photocatalysts with copper(I) or copper(II) salts has emerged as an efficient dual catalytic system for cross-coupling reactions.


2021 ◽  
Author(s):  
Tai-Chu Lau ◽  
Jing Xiang ◽  
Peng Ming ◽  
PAN Yi ◽  
Li-Juan Luo ◽  
...  

N-Dealkylation of amines by metal oxo intermediates (M=O) is related with drug detoxification and DNA repair in biological systems. In this study, we report the first example of N-dealkylation of...


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