Coupling Reactions on Secondary Allylic, Propargylic, and Alkyl Carbons Using Organoborates/Ni and RMgX/Cu Reagents

Enantiospecific, regioselective cross-coupling reactions of secondary allylic boronic esters.

Reactions in water: alkyl nitrile coupling reactions using Fenton's reagent.

The coupling reaction of water-soluble alkyl nitriles using Fenton's reagent (Fe(II) and H2O2) is described. The best metal for the reaction is iron(II), and the greatest yields are obtained when the concentration of the metal is kept low. Hydrogen-atom abstraction is selective, preferentially producing the radical alpha to the nitrile. In order to increase the production of dinitrile, in situ ...

Alkyl-alkyl Suzuki cross-coupling of unactivated secondary alkyl chlorides.

The first method for achieving alkyl–alkyl Suzuki reactions of unactivated secondary alkyl chlorides has been developed. Carbon–carbon bond formation occurs under mild conditions (at room temperature) with the aid of commercially available catalyst components. This method has proved to be versatile: without modification, it can be applied to Suzuki reactions of secondary and primary alkyl bromi...

Nickel-catalyzed cross-coupling reactions involving secondary and tertiary alkyl nucleophiles

Mechanistic insights into nickamine-catalyzed alkyl-alkyl cross-coupling reactions.

Within the last decades the transition metal-catalyzed cross-coupling of non-activated alkyl halides has significantly progressed. Within the context of alkyl-alkyl cross-coupling, first row transition metals spanning from iron, over cobalt, nickel, to copper have been successfully applied to catalyze this difficult reaction. The mechanistic understanding of these reactions is still in its infa...