2042-85-5Relevant articles and documents
Synthesis of Biaryl, Arylamine and Aryl Ketone Compounds Using a Commercially Available Air- and Moisture-Stable Palladium Catalyst
Marion, Nicolas,Navarro, Oscar,Kelly III, Roy A.,Nolan, Steven P.
, p. 2590 - 2592 (2003)
A commercially available palladium complex bearing a N-heterocyclic carbene (NHC) was used in gram-scale synthesis of three compounds, a biaryl, an arylamine and an aryl ketone. The syntheses were performed in catalytic fashion using a Suzuki-Miyaura, a B
Highly Ambiphilic Room Temperature Stable Six-Membered Cyclic (Alkyl)(amino)carbenes
Weinstein, Cory M.,Junor, Glen P.,Tolentino, Daniel R.,Jazzar, Rodolphe,Melaimi, Mohand,Bertrand, Guy
, p. 9255 - 9260 (2018)
Cyclic (alkyl)(amino)carbenes with a six-membered backbone were prepared. Compared to their five-membered analogues, they feature increased %Vbur and enhanced donor and acceptor properties, as evidenced by the observed n → π? transition trailin
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Ashby,E.C. et al.
, p. 1221 - 1232 (1979)
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A comparative mechanistic analysis of the stereoselectivity trends observed in the oxidation of chiral oxazolidinone-functionalized enecarbamates by singlet oxygen, ozone, and triazolinedione
Sivaguru,Poon, Thomas,Hooper, Catherine,Saito, Hideaki,Solomon, Marissa R.,Jockusch, Steffen,Adam, Waldemar,Inoue, Yoshihisa,Turro, Nicholas J.
, p. 10647 - 10659 (2006)
The stereoselectivity in the reactions of the E/Z enecarbamates 1, equipped with the oxazolidinone chiral auxiliary, has been examined for singlet oxygen (1O2), ozone (O3), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in
Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: A quaternary carbon atom makes the difference
Lavallo, Vincent,Canac, Yves,Praesang, Carsten,Donnadieu, Bruno,Bertrand, Guy
, p. 5705 - 5709 (2005)
(Chemical Equation Presented) Like NHCs? Not quite: Cyclic (alkyl)-(amino)carbenes (CAACs) are strong σ-donors and have steric environments that differ dramatically from those of bulky, electron-rich phosphines (A) and cyclic diaminocarbenes (B). These re
Anodic oxidation triggered divergent 1,2- And 1,4-group transfer reactions of β-hydroxycarboxylic acids enabled by electrochemical regulation
Jiang, Yangye,Lu, Gang,Mo, Fanyang,Yang, Jianxin,Yang, Yang,Yin, Yunxing,Zeng, Chengchu,Zhang, Lei,Zhang, Xianhao,Zhang, Zhenxing
, p. 12021 - 12028 (2020)
We report a set of electrochemically regulated protocols for the divergent synthesis of ketones and β-keto esters from the same β-hydroxycarboxylic acid starting materials. Enabled by electrochemical control, the anodic oxidation of carboxylic acids proceeded in either a one-electron or a two-electron pathway, leading to a 1,4-aryl transfer or a semipinacol-type 1,2-group transfer product with excellent chemoselectivity. The 1,4-aryl transfer represents an unprecedented example of carbon-to-oxygen group transfer proceeding via a radical mechanism. In contrast to previously reported radical group transfer reactions, this 1,4-group transfer process features the migration of electron-rich aryl substituents. Furthermore, with these chemoselective electrochemical oxidation protocols, a range of ketones and β-keto esters including those possessing a challenging-to-access medium-sized ring could be synthesized in excellent yields. This journal is
LIGANDS FOR TRANSITION METAL CATALYSTS
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Page/Page column 35-36, (2021/07/17)
Provided herein are a new class of extremely sterically-bulky, easily prepared N-heterocyclic carbene (NHC) ligands of Formula I, or a salt, solvate, geometric isomer, or stereoisomer thereof. The ligands are readily synthetically accessible exploiting the cost-effective, modular alkylation of anilines, an industrial chemical that is available in bulk. The NHC ligands form effective catalysts with transition metals such as Pd.
Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature
Venkatesh, Rapelly,Singh, Adesh Kumar,Lee, Yong Rok,Kandasamy, Jeyakumar
, p. 7832 - 7837 (2021/09/28)
Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.