Iron-Catalyzed Ligand-Free Carbon-Selenium (or Tellurium) Coupling of Arylboronic Acids with Diselenides and Ditellurides

2009 ◽  
Vol 351 (10) ◽  
pp. 1586-1594 ◽  
Author(s):  
Min Wang ◽  
Kai Ren ◽  
Lei Wang
Keyword(s):  
Free Carbon ◽  
Arylboronic Acids ◽  
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.

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

Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon–Carbon/Carbon–Nitrogen Bond-Forming Reactions

2020 ◽  
Vol 22 (18) ◽  
pp. 7244-7249
Author(s):  
Toshiki Akiyama ◽  
Yuki Wada ◽  
Makito Yamada ◽  
Yasunori Shio ◽  
Tetsuo Honma ◽  
...  
Keyword(s):  
Free Carbon ◽  
Bond Forming ◽  
Ligand Free ◽  
Bond Forming Reactions ◽  
Self Assembled ◽  
Nitrogen Bond ◽  
Nanoparticle Catalyst

ChemInform Abstract: Ligand-Free Copper-Catalyzed Coupling of Nitroarenes with Arylboronic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (34) ◽  
pp. no-no
Author(s):  
Jilei Zhang ◽  
Jiuxi Chen ◽  
Miaochang Liu ◽  
Xingwang Zheng ◽  
Jinchang Ding ◽  
...  
Keyword(s):  
Arylboronic Acids ◽  
Ligand Free

Base promoted highly efficient copper fluorapatite catalyzed coupling of phenols with arylboronic acids under mild and ligand-free conditions

RSC Advances ◽  
2012 ◽  
Vol 2 (33) ◽  
pp. 12818 ◽  
Author(s):  
Shafeek A. R. Mulla ◽  
Suleman M. Inamdar ◽  
Mohsinkhan Y. Pathan ◽  
Santosh S. Chavan
Keyword(s):  
Arylboronic Acids ◽  
Highly Efficient ◽  
Ligand Free
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