Journal ArticleDOI
Copper-Catalyzed Radical/Radical C sp 3H/PH Cross-Coupling: α-Phosphorylation of Aryl Ketone O-Acetyloximes†
TLDR
In this paper, a copper-catalyzed radical/radical C sp 3H/PH cross-coupling has been developed, which provides a radical/ radical cross coupling in a selective manner, in which aryl ketone o-acetyloximes and phosphine oxides were suitable for this transformation.Abstract:
The selective radical/radical cross-coupling of two different organic radicals is a great challenge due to the inherent activity of radicals. In this paper, a copper-catalyzed radical/radical C sp 3H/PH cross-coupling has been developed. It provides a radical/radical cross-coupling in a selective manner. This work offers a simple way toward β-ketophosphonates by oxidative coupling of aryl ketone o-acetyloximes with phosphine oxides using CuCl as catalyst and PCy3 as ligand in dioxane under N2 atmosphere at 130 °C for 5 h, and yields ranging from 47 % to 86 %. The preliminary mechanistic studies by electron paramagnetic resonance (EPR) showed that, 1) the reduction of ketone o-acetyloximes generates iminium radicals, which could isomerize to α-sp3-carbon radical species; 2) phosphorus radicals were generated from the oxidation of phosphine oxides. Various aryl ketone o-acetyloximes and phosphine oxides were suitable for this transformation.read more
Citations
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Journal ArticleDOI
Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?
TL;DR: This Review compares classical and photocatalytic procedures for selected classes of reactions and highlights their advantages and limitations.
Journal ArticleDOI
Photokatalyse mit sichtbarem Licht: Welche Bedeutung hat sie für die organische Synthese?
Journal ArticleDOI
A Visible-Light-Driven Iminyl Radical-Mediated C-C Single Bond Cleavage/Radical Addition Cascade of Oxime Esters.
TL;DR: A room-temperature, visible-light-driven N-centered iminyl radical-mediated and redox-neutral C-C single bond cleavage/radical addition cascade reaction of oxime esters and unsaturated systems has been accomplished, enabling highly selective formation of various chemical bonds.
Journal ArticleDOI
Monofluoroalkenylation of Dimethylamino Compounds through Radical-Radical Cross-Coupling.
TL;DR: The striking features of this redox-neutral method in terms of scope, functional-group tolerance, and regioselectivity are illustrated by the late-stage fluoroalkenylation of complex molecular architectures such as bioactive (+)-diltiazem, rosiglitazone, dihydroartemisinin, oleanic acid, and androsterone derivatives.
Journal ArticleDOI
Internal Oxidant-Triggered Aerobic Oxygenation and Cyclization of Indoles under Copper Catalysis
TL;DR: Oximes as an internal oxidant have been demonstrated to be a driver to initiate aerobic oxidation, which provides a new oxidative pattern for C-H functionalization even with high atom- and step-economy.
References
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Journal ArticleDOI
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.
TL;DR: A review of palladium-catalyzed coupling of CH bonds with organometallic reagents through a PdII/Pd0 catalytic cycle can be found in this paper.
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Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds
Charles S. Yeung,Vy M. Dong +1 more
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Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.
TL;DR: A number of improvements have developed the former process into an industrially very useful and attractive method for the construction of aryl -aryl bonds, but the need still exists for more efficient routes whereby the same outcome is accomplished, but with reduced waste and in fewer steps.
Journal ArticleDOI
Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.
TL;DR: This work over the past several years to form carbon-carbon bonds directly from two different C-H bonds under oxidative conditions, cross-dehydrogenative coupling (CDC) is described, which provides an alternative to the separate steps of prefunctionalization and defunctionsalization that have traditionally been part of synthetic design.