ABSTRACT
A nickel-catalyzed cross-coupling reaction of aryl methyl sulfides with aryl bromides has been developed to access biaryls in yields of up to 86%. The reactions proceeded well using Ni(COD)2 as catalyst with the ligand BINAP (2,2'-bis(diphenylphosphanyl)-1,1'-binaphthalene) in the presence of magnesium. The method has a broad scope of substrates and is scalable. The wide availability of commercially available aryl bromides and the absence of preparation and preparation of organometallic reagents make the reaction of high application value.
ABSTRACT
A palladium-catalyzed cyanation of aryl dimethylsulfonium salts using cheap, nontoxic, and bench-stable K4[Fe(CN)6]·3H2O as the cyanating reagent has been developed. The reactions proceeded well under base-free conditions with various sulfonium salts and provided aryl nitrile with yields of up to 92%. Aryl sulfides can be transformed to aryl nitriles directly via a one-pot process, and the protocol is scalable. Density functional theory calculations were performed to investigate the reaction mechanism that involved a catalytic cycle involving oxidative addition, ligand exchange, reductive elimination, and regeneration to yield the product.
Subject(s)
Palladium , Salts , Molecular Structure , Nitriles , CatalysisABSTRACT
An efficient protocol for synthesis of thioamides was developed via the microwave-assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines. This process is scalable and tolerates a wide spectrum of amines to deliver the corresponding products in moderate to excellent yields in 10 minutes, providing a cheap and rapid approach to thioamides.
