Dehydrocoupling reactions between the boranes HBpin and 9-borabicyclo[3.3.1]nonane and a range of amines and anilines ensue under very mild reaction conditions in the presence of a simple β-diketiminato magnesium n-butyl precatalyst. The facility of the reactions is suggested to be a function of the Lewis acidity of the borane substrate, and is dictated by resultant pre-equilibria between, and ...

The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)2 as catalyst to give the desired products in up to 71% yield. Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the correspon...

Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bond-donating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bond-accepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the...

Chiral 4-[(2-isopropyl-5-methylcyclohexyl)oxo]-4oxobutanoic acid reacts with substituted anilines to produce amides 1-6 in high yields. Resulted amides 1-6 were investigated for their antifungal and antibacterial activities. Compounds 2 (96.5%) against Aspergillus fumigatus and 6 (93.7%) against Helminthosporium sativum demonstrated excellent activities. However, compounds 3 (37.6%) against Bac...

a simple and mild procedure for the conversion of anilines into aryl isocyanates is described using the 3-hydroxypropylammonium acetate (hpaa) ionic liquid as a novel and efficient media has been explored in the synthesis of aryl isocyanates from the reaction of substituted urea with sodium nitrite in a water immiscible solvent. this ionic liquid can be easily recovered and reused for many time...

The reduction of nitroarenes to anilines as well azobenzenes hydrazobenzenes using a single base-metal catalyst is reported. hydrogenation reactions are performed with an air-and moisture-stable manganese and proceed under relatively mild reaction conditions. transformation tolerates broad range functional groups, affording aniline derivatives in high yields. Mechanistic studies suggest that th...

The rhodium-catalyzed regio- and enantioselective amination of racemic tertiary allylic trichloroacetimidates with a variety of aniline nucleophiles is a direct and efficient route to chiral α,α-disubstituted allylic N-arylamines. We describe the first dynamic kinetic asymmetric transformations of racemic tertiary allylic electrophiles with anilines utilizing a chiral diene-ligated rhodium cata...

Substituted 4-hydroxyquinolines were synthesized from anilines and diethyl 2-(ethoxymethylene)malonate by the Gould-Jacobs reaction via cyclization of the intermediate anilinomethylenemalonate followed by hydrolysis and decarboxylation. The 4-hydroxyquinolines reacted with phosphorous oxychloride to form 4-chloroquinolines, which reacted on heating with diethyl sodiomethylmalonate in DMF to yie...

Single-step reduction of aryl nitro and carbonyl groups to the corresponding synthetically useful alkyl-anilines occurs with excellent yields by treatment with hydrazine and a base in a solvent-free reaction. The method has been applied to a broad range of compounds with different properties. Investigations into the mechanism of the reduction reveal that each group is reduced independently. A m...