ChemInform Abstract: Ligand-Free PdCl2-Catalyzed Heck Reaction of Arylboronic Acids and Olefins under Reusable TBAB/H2O Conditions.

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2014 ◽  
Vol 45 (13) ◽  
pp. no-no
Author(s):  
Bo-Xiao Tang ◽  
Xiao-Niu Fang ◽  
Ren-Yun Kuang ◽  
Rong-Hua Hu ◽  
Ji-Wei Wang ◽  
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Jinchang Ding ◽  
Jun Jiang ◽  
Jiuxi Chen ◽  
Huayue Wu ◽  
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2013 ◽  
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pp. 2971-2976 ◽  
Author(s):  
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Xiao-Niu Fang ◽  
Ren-Yun Kuang ◽  
Rong-Hua Hu ◽  
Ji-Wei Wang ◽  
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Ashis Kumar Jena ◽  
Dibya Das ◽  
Swagatika Sahu ◽  
Rajesh Kumar Singh

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
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Lucille A. Wells ◽  
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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.


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

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