The biaryl structural motif is a predominant feature in many pharmaceutically relevant and biologically active compounds. As a result, for over a century1 organic chemists have sought to develop new and more efficient aryl-aryl bond-forming methods. Although there exist a variety of routes for the construction of aryl-aryl bonds, arguably the most common method is through the use of transition-...

Kinetic studies conducted under both catalytic and stoichiometric conditions were employed to investigate the reductive elimination of RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl) based palladium amido complexes. These complexes were found to be the resting state in Pd-catalyzed cross-coupling reactions for a range of aryl halides and diarylamines. Hammett plots demonstrated that...

An efficient site selective method for the direct arylation of free-(NH2) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH)2/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time che...

The oxidative treatment of vinyltris(trimethylsilyl)germanes with hydrogen peroxide (NaOH/H(2)O/THF) or tert-butyl peroxide (KH/THF) generates reactive germanol or germanoxane species that undergo Pd-catalyzed cross-couplings with aryl and alkenyl halides and aryl triflates in the presence of Pd(PPh(3))(4). Vinylgermanes having either a conjugated or isolated double bond serve as versatile tran...

Important aspects of the electrochemical reduction of aryl thiocyanates were investigated. A striking change in the reductive cleavage mechanism as a function of the substituent on the aryl ring of the aryl thiocyanate is observed. A similar behavior has been reported for benzyl halides. This is different from what is widely reported for aryl halides where a stepwise mechanism is taking place r...

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize reaction media, and not tolerant multi-step transformations. Here we introduce base-activated, latent reagents: β-nitrile β-ester sulfones. We show that under the conditions, these species generate salt...

poly (vinylpyrrolidone)-grafted silica as an organic-inorganic hybrid material was used as an effective heterogeneous polymeric cosolvent catalyst in organic reactions. this modified silica catalyzed nucleophilic displacement of alkyl halides for easy preparation of alkyl thiocyanates, alkyl cyanides, alkyl azides and alkyl aryl ethers. furthermore, the catalyst was applied for the conversion o...

Suzuki cross-coupling reaction of different aryl halides with arylboronic acids was successfully carried out in methanol using ortho-palladated complex of 2-methoxyphenethylamine. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of this complex as efficient and active catalyst. Application of microwave irradiation improved the yields of th...

The one-pot synthesis of symmetrical triaryl amines using aryl halides and 5-Methyl-1,3,4-Thiadiazole-2-Amine as a nitrogen-transfer reagent is reported. Copper oxide nanoparticles that does not require the presence of any additional ligand, improved rate and facility of the synthesis of triaryl amines. The introduction of a new N-source, using green solvents PEG/H2O, normal atmospheric conditi...

Suzuki cross-coupling reaction of different aryl halides with arylboronic acids was successfully carried out in methanol using ortho-palladated complex of 2-methoxyphenethylamine. All substrates afforded the corresponding products in good to high yields in the presence of low amounts of this complex as efficient and active catalyst. Application of microwave irradiation improved the yields of th...