Intramolecular Pd-catalyzed alkene carboamination reactions of substituted 2-allyl-N-(2-bromobenzyl)anilines are described. The substrates for these reactions are generated in two steps from readily available 2-allylanilines and 2-bromobenzaldehyde derivatives. The transformations afford substituted tetrahydroindoloisoquinolines, an uncommon class of fused bicyclic heterocycles, in good yield. ...

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and...

The prevalence of indoles in bioactive molecules has prompted the development of many useful methods for their preparation. Despite advances, most of these techniques rely heavily on substrate preactivation, and very few employ readily available anilines as starting materials. Transition metal catalyzed processes are illustrative, commonly requiring ortho-halogenated anilines as starting materi...

An expeditious assembling of fused poly-heterocyclic structures having a N(Acyl), N(aryl)-Acetal core has been accomplished by cascade reaction ortho-functionalized anilines with 2-formylbenzonitrile and subsequent intramolecular N-amidic cyclization on different electrophilic carbons. The syntheses have finalized using both cathodically-initiated conventional base-catalyzed methods comparing t...

We report a Chan–Lam coupling reaction of benzylic and allylic boronic esters with primary secondary anilines to form valuable alkyl amine products. Both tertiary can be used as partners, mono-alkylation the aniline occurring selectively. This is rare example transition-metal-mediated transformation alkylboron reagent. Initial investigation into mechanism suggests that transmetalation from B Cu...