Control of Chemo-, Regio-, and Stereoselectivities in Ligand-Free Pd-Catalyzed Oxidative Heck Reactions of Arylboronic Acids or Alkenylboronate with Allyl Esters

2009 ◽  
Vol 11 (14) ◽  
pp. 2980-2983 ◽  
Author(s):  
Yijin Su ◽  
Ning Jiao
Keyword(s):  
Heck Reactions ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Allyl Esters

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.

Continuous Flow Palladium(II)-Catalyzed Oxidative Heck Reactions with Arylboronic Acids

2010 ◽  
Vol 2010 (12) ◽  
pp. 2270-2274 ◽  
Author(s):  
Luke R. Odell ◽  
Jonas Lindh ◽  
Tomas Gustafsson ◽  
Mats Larhed
Keyword(s):  
Continuous Flow ◽  
Heck Reactions ◽  
Arylboronic Acids

ChemInform Abstract: Base Promoted Highly Efficient Copper Fluorapatite Catalyzed Coupling of Phenols with Arylboronic Acids under Mild and Ligand-Free Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (16) ◽  
pp. no-no
Author(s):  
Shafeek A. R. Mulla ◽  
Suleman M. Inamdar ◽  
Mohsinkhan Y. Pathan ◽  
Santosh S. Chavan
Keyword(s):  
Arylboronic Acids ◽  
Highly Efficient ◽  
Ligand Free

Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids

Synlett ◽  
2016 ◽  
Vol 28 (05) ◽  
pp. 601-606 ◽  
Author(s):  
Feng Gao ◽  
Xian-Li Zhou ◽  
Ya-Nan Cao ◽  
Xin-Chuan Tian ◽  
Xing-Xiu Chen ◽  
...  
Keyword(s):  
Free Base ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Homocoupling Reaction

scholarly journals Ligand-free Heck reactions using low Pd-loading

2004 ◽  
pp. 1559 ◽  
Author(s):  
Manfred T. Reetz ◽  
Johannes G. de Vries
Keyword(s):  
Heck Reactions ◽  
Ligand Free

Highly Efficient and Reusable Polyaniline-Supported Palladium Catalysts for Open-Air Oxidative Heck Reactions under Base- and Ligand-Free Conditions

2008 ◽  
Vol 350 (13) ◽  
pp. 1968-1974 ◽  
Author(s):  
Pravin R. Likhar ◽  
Moumita Roy ◽  
Sarabindu Roy ◽  
M. S. Subhas ◽  
M. Lakshmi Kantam ◽  
...  
Keyword(s):  
Palladium Catalysts ◽  
Heck Reactions ◽  
Supported Palladium Catalysts ◽  
Highly Efficient ◽  
Ligand Free ◽  
Supported Palladium
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