Phosphine Ligand‐Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

ChemCatChem ◽  
2019 ◽  
Vol 11 (10) ◽  
pp. 2500-2510 ◽  
Author(s):  
Bin Guo ◽  
Tian‐Qi Yu ◽  
Hong‐Xi Li ◽  
Shi‐Qi Zhang ◽  
Pierre Braunstein ◽  
...  
Keyword(s):  
Ruthenium Complexes ◽  
Phosphine Ligand ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Ligand Free

Dendrimer-encapsulated Pd(0) nanoparticles immobilized on nanosilica as a highly active and recyclable catalyst for the copper- and phosphine-free Sonogashira–Hagihara coupling reactions in water

2016 ◽  
Vol 6 (11) ◽  
pp. 4005-4019 ◽  
Author(s):  
Mohsen Esmaeilpour ◽  
Alireza Sardarian ◽  
Jaber Javidi
Keyword(s):  
Phosphine Ligand ◽  
Recyclable Catalyst ◽  
Coupling Reactions ◽  
Highly Active ◽  
Ligand Free

Recyclable dendrimer-encapsulated Pd(0) nanoparticles immobilized on nanosilica in the Sonogashira–Hagihara reaction under copper(i) and phosphine ligand-free conditions in water.

Transition-Metal-Free Synthetic Strategies for the Cross-Coupling Reactions in Water: A Green Approach

2020 ◽  
Vol 07 ◽  
Author(s):  
Tanmay Chatterjee ◽  
Nilanjana Mukherjee
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Aqueous Media ◽  
Cross Coupling ◽  
Transition Metal Catalysts ◽  
Synthetic Methods ◽  
Coupling Reactions ◽  
Organic Transformations ◽  
Green Approach ◽  
Dehydrogenative Coupling

Abstract: A natural driving force is always working behind the synthetic organic chemists towards the development of ‘green’ synthetic methodologies for the synthesis of useful classes of organic molecules having potential applications. The majority of the essential classes of organic transformations, including C-C and C-X (X = heteroatom) bond-forming crosscoupling reactions, cross dehydrogenative-coupling (CDC) mostly rely on the requirement of transition-metal catalysts and hazardous organic solvents. Hence, the scope in developing green synthetic strategies by avoiding the use of transitionmetal catalysts and hazardous organic solvents for those important and useful classes of organic transformations is very high. Hence, several attempts are made so far. Water being the most abundant, cheap, and green solvent in the world; numerous synthetic methods have been developed in an aqueous medium. In this review, the development of transitionmetal- free green synthetic strategies for various important classes of organic transformations such as C-C and C-X bondforming cross-coupling, cross dehydrogenative-coupling, and oxidative-coupling in an aqueous media is discussed.

Ruthenium-catalyzed synthesis of N-substituted lactams by acceptorless dehydrogenative coupling of diols with primary amines

2019 ◽  
Vol 55 (82) ◽  
pp. 12384-12387 ◽  
Author(s):  
Yanling Zheng ◽  
Xufeng Nie ◽  
Yang Long ◽  
Li Ji ◽  
Haiyan Fu ◽  
...  
Keyword(s):  
Phosphine Ligand ◽  
Primary Amines ◽  
Dehydrogenative Coupling ◽  
One Step

The first synthesis of N-substituted lactams via an acceptorless dehydrogenative coupling of diols with primary amines in one step was enabled by combining Ru3(CO)12 with a hybrid N-heterocyclic carbene–phosphine–phosphine ligand as the catalyst.

scholarly journals Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Cong Wang ◽  
Hui Zhang ◽  
Lucille A. Wells ◽  
Tian Liu ◽  
Tingting Meng ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom Abstraction ◽  
Coupling Reactions ◽  
Ambient Light ◽  
Environmental Friendliness ◽  
Copper Species ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Byproduct Formation ◽  
Electron Reduction

AbstractN-Arylation of NH-sulfoximines represents an appealing approach to access N-aryl sulfoximines, but has not been successfully applied to NH-diaryl sulfoximines. Herein, a copper-catalyzed photoredox dehydrogenative Chan-Lam coupling of free diaryl sulfoximines and arylboronic acids is described. This neutral and ligand-free coupling is initiated by ambient light-induced copper-catalyzed single-electron reduction of NH-sulfoximines. This electron transfer route circumvents the sacrificial oxidant employed in traditional Chan-Lam coupling reactions, increasing the environmental friendliness of this process. Instead, dihydrogen gas forms as a byproduct of this reaction. Mechanistic investigations also reveal a unique autocatalysis process. The C–N coupling products, N-arylated sulfoximines, serve as ligands along with NH-sulfoximine to bind to the copper species, generating the photocatalyst. DFT calculations reveal that both the NH-sulfoximine substrate and the N-aryl product can ligate the copper accounting for the observed autocatalysis. Two energetically viable stepwise pathways were located wherein the copper facilitates hydrogen atom abstraction from the NH-sulfoximine and the ethanol solvent to produce dihydrogen. The protocol described herein represents an appealing alternative strategy to the classic oxidative Chan-Lam reaction, allowing greater substrate generality as well as the elimination of byproduct formation from oxidants.

Tunable Ligand Effects on Ruthenium Catalyst Activity for Selectively Preparing Imines or Amides by Dehydrogenative Coupling Reactions of Alcohols and Amines

2017 ◽  
Vol 23 (52) ◽  
pp. 12795-12804 ◽  
Author(s):  
Takafumi Higuchi ◽  
Risa Tagawa ◽  
Atsuhiro Iimuro ◽  
Shoko Akiyama ◽  
Haruki Nagae ◽  
...  
Keyword(s):  
Catalyst Activity ◽  
Ruthenium Catalyst ◽  
Coupling Reactions ◽  
Ligand Effects ◽  
Dehydrogenative Coupling

One Pot Tandem Dual C=C and C=O Bond Reductions in β-Alkylation of Secondary Alcohols with Primary Alcohols by Ruthenium Complexes of Amido and Picolyl Functionalized N-Heterocyclic Carbenes

2021 ◽  
Author(s):  
A. P. Prakasham ◽  
Sabyasachi Ta ◽  
Shreyata Dey ◽  
Prasenjit Ghosh
Keyword(s):  
Ruthenium Complexes ◽  
Heterocyclic Carbenes ◽  
Secondary Alcohols ◽  
Coupling Reactions ◽  
Primary Alcohols ◽  
One Pot ◽  
The One ◽  
Alcohol Alcohol

Two different class of ruthenium complexes, namely, [1-mesityl-3-(2,6-Me2-phenylacetamido)-imidazol-2-ylidene]Ru(p-cymene)Cl (1c) and {[1-(pyridin-2-ylmethyl)-3-(2,6-Me2-phenyl)-imidazol-2-ylidene]Ru(p-cymene)Cl}Cl (2c), successfully carried out the one-pot tandem alcohol-alcohol coupling reactions of a variety of secondary and primary alcohols, in...

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