Samarium Powder-Catalyzed Palladium-Free and Ligand-Free Sonogashira Coupling Reactions

2009 ◽  
Vol 351 (13) ◽  
pp. 2101-2106 ◽  
Author(s):  
Jincheng Mao ◽  
Minyan Wu ◽  
Guanlei Xie ◽  
Shunjun Ji
Keyword(s):  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Ligand Free

PEPPSI-SONO-SP2: a new highly efficient ligand-free catalyst system for the synthesis of tri-substituted triazine derivatives via Suzuki–Miyaura and Sonogashira coupling reactions under a green approach

2016 ◽  
Vol 40 (6) ◽  
pp. 5135-5142 ◽  
Author(s):  
Motakatla Venkata Krishna Reddy ◽  
Peddiahgari Vasu Govardhana Reddy ◽  
Cirandur Suresh Reddy
Keyword(s):  
Palladium Catalyst ◽  
Cross Coupling ◽  
Catalyst System ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Green Approach ◽  
Ligand Free ◽  
Triazine Derivatives

Consecutive Suzuki–Miyaura and Sonogashira cross coupling reactions catalyzed by a new competent palladium catalyst PEPPSI-SONO-SP2 under mild and green reaction conditions.

ChemInform Abstract: Ligand-Free Sonogashira Coupling Reactions with Heterogeneous Pd/C as the Catalyst.

ChemInform ◽  
2008 ◽  
Vol 39 (49) ◽  
Author(s):  
Shigeki Mori ◽  
Takayoshi Yanase ◽  
Satoka Aoyagi ◽  
Yasunari Monguchi ◽  
Tomohiro Maegawa ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Ligand Free

Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions

2007 ◽  
Vol 48 (49) ◽  
pp. 8761-8764 ◽  
Author(s):  
Andrea Biffis ◽  
Elena Scattolin ◽  
Nicoletta Ravasio ◽  
Federica Zaccheria
Keyword(s):  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Ligand Free

ChemInform Abstract: Samarium Powder-Catalyzed Palladium-Free and Ligand-Free Sonogashira Coupling Reactions.

ChemInform ◽  
2010 ◽  
Vol 41 (3) ◽  
Author(s):  
Jincheng Mao ◽  
Minyan Wu ◽  
Guanlei Xie ◽  
Shunjun Ji
Keyword(s):  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Ligand Free

Ligand-Free Sonogashira Coupling Reactions with Heterogeneous Pd/C as the Catalyst

2008 ◽  
Vol 14 (23) ◽  
pp. 6994-6999 ◽  
Author(s):  
Shigeki Mori ◽  
Takayoshi Yanase ◽  
Satoka Aoyagi ◽  
Yasunari Monguchi ◽  
Tomohiro Maegawa ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Ligand Free

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.

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