Reusable and Magnetic Palladium and Copper Oxide Catalysts in Direct ortho and meta Arylation of Anilide Derivatives
We report a general, direct C-H arylation of anilide derivatives using reusable palladium or copper oxide on magnetite as heterogeneous precatalysts. Highly selective ortho and meta arylations are achieved using electronically and sterically diverse diaryliodonium salts. Catalytically active soluble species from the heterogeneous precursors were detected by experimental techniques. Preliminary mechanistic investigation suggests different reaction pathways for each of the catalysts.
Vásquez-Céspedes, Suhelen,Holtkamp, Michael,Karst, Uwe,Glorius, Frank
supporting information
p. 2759 - 2764
(2017/12/14)
PROCESS FOR PREPARING BIPHENYLAMINES FROM ANILIDES BY RUTHENIUM CATALYSIS
The present invention relates to a novel process for preparing substituted biphenylamides of the general formula (V) characterized in that anilides of the formula (II) in a solvent other than tetrahydrofuran, are reacted with an organoboron compound of the formula (III) in the presence of a catalyst system consisting of a ruthenium catalyst, an activator, an oxidizing agent and a metal triflate.
-
Page/Page column 33-34
(2016/11/28)
One pot synthesis of phenanthridines using a palladium-catalyzed cyclization of aromatic ketoximes with aryl iodides: Via Beckmann rearrangement
The catalytic reaction of ketoximes with aryl iodides via a Beckmann rearrangement in the presence of a catalytic amount of Pd(OAc)2, Ag2O and ZnBr2 gave substituted phenanthridines in good to excellent yield. In the reaction, aromatic ketoximes converted first to acetanilides in the presence of ZnBr2/TFA via a Beckmann rearrangement followed by arylation in the presence of palladium complex. Furthermore, ortho-arylated acetanilides were converted to phenanthridine derivatives in the presence of a Hendrickson reagent.
Ruthenium(II)-catalyzed C-H arylation of anilides with boronic acids, borinic acids and potassium trifluoroborates
An in situ generated cationic ruthen-ium(II) catalyst allowed for robust C-H arylations of anilides with boronic acids. The optimized ruthenium catalyst was found to be both site selective and chemoselective, thereby providing the monoarylated products in
Rhodium(III)-catalyzed ortho-arylation of anilides with aryl halides
An efficient o-arylation of pivalamides by aryl iodides via rhodium(III)-catalyzed C-H activation is demonstrated for the first time. Further, the biaryl products can be converted effectively into biologically active phenanthridine and phenanthridinone derivative.