A direct convergent two-component synthesis of quinolines from alpha,beta-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup-Doebner-Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates prepared by direct palladium-catalyzed borylation of the corresponding o-bromoanilines.

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Abstract:The combination of an air-stable iridium catalyst and the dipolar aprotic solvent dimethyl sulfoxide (DMSO) allowed, for the first time, the systematic exploitation of highly polar, functionalized amines in asymmetric allylic substitutions: low molecular weight, sp 3 -rich chiral building blocks were obtained with physicochemical properties that will be valuable in the synthesis of lead-like small molecules.

Unexpectedly high retention times were obtained in HPLC investigations for compounds equipped with (C 8 F 17 CH 2 CH 2 ) 3 Si tags on C 8 F 17 -modified silica gel (Fig. 4). Hence, these tags have a high potential for the noncovalent immobilization of catalysts to be applied in organic solvents, allowing for an easy separation and reuse of the catalyst by filtration and reapplication. The tris(perfluoroalkyl)silyl tag could be incorporated in a straightforward manner into ligands as demonstrated by the synthesis of several prominent classes of ligands (Schemes 4 ± 6).