Nickel‐Catalyzed Cross‐Coupling of Aryltrimethylammonium Iodides with Organozinc Reagents

Abstract

Broad scope and good tolerance: An efficient cross‐coupling of aryltrimethylammonium iodide salts with aryl‐, methyl‐, and benzylzinc chlorides catalyzed by [Ni(PCy3)2Cl2] has been achieved (see scheme). The reaction involves cleavage of the CN bond and displays broad substrate scope and good functional group tolerance. NMP=N‐methylpyrrolidine.

Nickel-Catalyzed Cross Couplings of Benzylic Ammonium Salts and Boronic Acids: Stereospecific Formation of Diarylethanes via C–N Bond Activation

“…11 Using conditions similar to those reported for Suzuki reactions of aryl ammonium salts, 13a low yields of diarylmethane 2 were observed when iodide 1a was employed (Table 1, entry1). In contrast, use of monodentate phosphine ligands, particularly mixed aryl/alkyl phosphines, provided increased yields (entries 2–4).…”

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

“…[4] Besides TM-catalysed CÀCbond-forming reactions, fluorination of aryl CÀNbonds in ammonium salts through an S N Ar mechanism has also been reported, [5] and is now used for labeling bioactive molecules with 18 F. However,a lthough oxygen is an electronegative element like fluorine,t here are few reports on the reaction of ammonium salts with alcohols or phenols to afford ethers, despite the great utility that as uitable method would have. [4] Besides TM-catalysed CÀCbond-forming reactions, fluorination of aryl CÀNbonds in ammonium salts through an S N Ar mechanism has also been reported, [5] and is now used for labeling bioactive molecules with 18 F. However,a lthough oxygen is an electronegative element like fluorine,t here are few reports on the reaction of ammonium salts with alcohols or phenols to afford ethers, despite the great utility that as uitable method would have.…”

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO2 at room temperature

“…[1][2][3][4][5] Compared with other N-alkyl amines, N-methyl and N,Ndimethyl amines have attracted extensive attention in industry. [1][2][3][4][5] Compared with other N-alkyl amines, N-methyl and N,Ndimethyl amines have attracted extensive attention in industry.…”