ChemInform Abstract: Metal-Catalyzed Reductive Coupling Reactions of Organic Halides with Carbonyl-Type Compounds

ChemInform ◽  
2014 ◽  
Vol 45 (39) ◽  
pp. no-no
Author(s):  
Toni Moragas ◽  
Arkaitz Correa ◽  
Ruben Martin
Keyword(s):  
Coupling Reactions ◽  
Reductive Coupling ◽  
Organic Halides ◽  
Metal Catalyzed

DFT Study of the Mechanisms of Transition-Metal-Catalyzed Reductive Coupling Reactions

2020 ◽  
Vol 24 (12) ◽  
pp. 1367-1383
Author(s):  
Yuling Wang ◽  
Qinghua Ren
Keyword(s):  
Transition Metal ◽  
Density Functional ◽  
Single Point ◽  
Oxidative Addition ◽  
Density Functional Theory Calculations ◽  
Reductive Elimination ◽  
Coupling Reactions ◽  
Reductive Coupling ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

The mechanism studies of transition-metal-catalyzed reductive coupling reactions investigated using Density Functional Theory calculations in the recent ten years have been reviewed. This review introduces the computational mechanism studies of Ni-, Pd-, Cu- and some other metals (Rh, Ti and Zr)-catalyzed reductive coupling reactions and presents the methodology used in these computational mechanism studies. The mechanisms of the transition- metal-catalyzed reductive coupling reactions normally include three main steps: oxidative addition; transmetalation; and reductive elimination or four main steps: the first oxidative addition; reduction; the second oxidative addition; and reductive elimination. The ratelimiting step is most likely the final reductive elimination step in the whole mechanism. Currently, the B3LYP method used in DFT calculations is the most popular choice in the structural geometry optimizations and the M06 method is often used to carry out single-point calculations to refine the energy values. We hope that this review will stimulate more and more experimental and computational combinations and the computational chemistry will significantly contribute to the development of future organic synthesis reactions.

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.

End-functionalization of dithiarubicene: Modulation of optoelectronic properties by metal-catalyzed coupling reactions and device application

2021 ◽  
Author(s):  
Kenji Tsukamoto ◽  
Koji Takagi ◽  
Keitaro Yamamoto ◽  
Yutaka Ie ◽  
Takanori Fukushima
Keyword(s):  
Optoelectronic Properties ◽  
Coupling Reactions ◽  
Device Application ◽  
Metal Catalyzed ◽  
Structure Properties

In order to modulate optoelectronic properties of dithiarubicene (DTR) by the end-functionalization and reveal the structure-properties relationship in detail, we have carried out a set of metal-catalyzed coupling reactions. Electron-withdrawing...

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