Nickel-Copper Co-Catalyzed Sustainable Synthesis of Diaryl- Chalcogenides

2021 ◽  
Vol 08 ◽  
Author(s):  
Debasish Kundu ◽  
Anup Roy ◽  
Abhijit Singha ◽  
Subir Panja
Keyword(s):  
Low Cost ◽  
Cross Coupling ◽  
Catalytic Amount ◽  
Metal Catalyst ◽  
Coupling Reactions ◽  
Co Catalyst ◽  
Cross Coupling Reactions ◽  
Nickel Copper ◽  
Wide Range ◽  
Elimination Pathway

Abstract:: In recent times, Nickel has become a powerful alternative transition metal catalyst for performing cross-coupling reactions due to its low cost and better sustainability. Thus a sustainable Ni-catalyzed C-Se cross coupling has been developed in presence of catalytic amount of copper iodide as co-catalyst. A wide range of substituted diaryl selenides have been synthesized by this Ni-Cu dual catalyzed C-Se cross coupling. The reaction is following an oxidative addition and reductive elimination pathway where Cu is playing an important role in transmetalation. The mechanism of the reaction was established by several experimental techniques.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Synthesis ◽  
2021 ◽  
Author(s):  
Felipe C. Demidoff ◽  
Leandro L. de Carvalho ◽  
Eduardo José P. Rodrigues Filho ◽  
Andréa Luzia F. de Souza ◽  
Chaquip D. Netto
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Biological Activities ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Large Array ◽  
Terminal Alkyne ◽  
Co Catalyst ◽  
Cross Coupling Reactions ◽  
Convenient Synthesis

AbstractFunctionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free CuI-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.

scholarly journals Copper’s rapid ascent in visible-light photoredox catalysis

Science ◽  
2019 ◽  
Vol 364 (6439) ◽  
pp. eaav9713 ◽  
Author(s):  
Asik Hossain ◽  
Aditya Bhattacharyya ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Organic Dyes ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Photoredox Catalysis ◽  
Cross Coupling Reactions ◽  
Rapid Ascent ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

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.

scholarly journals Copper-Promoted Cross-Coupling Reactions for the Synthesis of Aryl(difluoromethyl)phosphonates Using Trimethylsilyl(difluoromethyl)phosphonate

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3292 ◽  
Author(s):  
Kazuki Komoda ◽  
Rei Iwamoto ◽  
Masakazu Kasumi ◽  
Hideki Amii
Keyword(s):  
Cross Coupling ◽  
Catalytic Amount ◽  
Coupling Reactions ◽  
Stoichiometric Amount ◽  
Cross Coupling Reactions ◽  
Aryl Iodides

A convenient and effective route for the synthesis of aryl(difluoromethyl)phosphonates has been developed based on cross-coupling reactions. Upon treatment with a stoichiometric amount (or a catalytic amount in some cases) of CuI and CsF, aryl iodides reacted smoothly with (silyldifluoromethyl)phosphonates to give the corresponding aryl(difluoromethyl)phosphonates in good yields.

scholarly journals Gram-Scale Synthesis of the N-Phenyl Phenothiazine Photocatalyst by Benzyne Addition

2021 ◽  
Author(s):  
Erin Welsh ◽  
Katherine Robertson ◽  
Alex Speed
Keyword(s):  
Transition Metal ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

N-phenyl phenothiazine is one of the most reducing photoredox catalysts. Its synthesis commonly requires transition metal catalyzed cross-coupling reactions. Here we show the syntheses of four aryl phenothiazines via a benzyne route, including a multi-gram scale synthesis of N-phenyl phenothiazine. While yields are modest, the simplicity, low cost, and lack of requirement for cross-coupling catalyst in this synthesis will be attractive to users of this photocatalyst.

Valorisation of urban waste to access low-cost heterogeneous palladium catalysts for cross-coupling reactions in biomass-derived γ-valerolactone

2021 ◽  
Author(s):  
Federica Valentini ◽  
Francesco Ferlin ◽  
Simone Lilli ◽  
Assunta Marrocchi ◽  
Liu Ping ◽  
...  
Keyword(s):  
Palladium Catalysts ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Urban Waste ◽  
Cross Coupling Reactions ◽  
Simple Protocol

Herein we report a simple protocol for the valorisation of a common urban biowaste.

Bifunctional property of Pt nanoparticles deposited on TiO2 for the photocatalytic sp3C–sp3C cross-coupling reactions between THF and alkanes

2017 ◽  
Vol 7 (12) ◽  
pp. 2616-2623 ◽  
Author(s):  
Akanksha Tyagi ◽  
Akira Yamamoto ◽  
Tatsuhisa Kato ◽  
Hisao Yoshida
Keyword(s):  
Pt Nanoparticles ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Coupling Reactions ◽  
Photoexcited Electron ◽  
Cross Coupling Reactions ◽  
Direct Cross

Photocatalytic direct cross-coupling between THF and alkanes was accelerated by Pt nanoparticles on TiO2, as a receiver for photoexcited electron and a metal catalyst.

A Highly Active Cobalt Catalyst System for Kumada Biaryl Cross-Coupling

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1199-1202 ◽  
Author(s):  
Wenqin Wu ◽  
Hung Duong
Keyword(s):  
Room Temperature ◽  
Cobalt Catalyst ◽  
Cross Coupling ◽  
Catalyst System ◽  
Coupling Reactions ◽  
Short Reaction Time ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Aryl Bromides ◽  
Wide Range

A highly active cobalt catalyst system has been developed for the cross-coupling reactions of arylmagnesium reagents and aryl bromides. In the presence of 1 mol% CoCl2, 2 mol% IPr·HCl and 2 mol% NaO t Bu, a wide range of (hetero)biaryls are prepared in 51–99% yields at room temperature within a short reaction time.

Sign in / Sign up

Export Citation Format

Share Document