Hydrovinylation

The addition can be done highly regio- and stereoselectively, although the choices of metal, ligands, and counterions often play very important role.

[6][7][8] In a stoichiometric version of a hydrovinylation reaction, nucleophiles add to an electrophilic transition metal alkene complex, forming a C-C bond.

An early example was provided by the Murai reaction, which involves the insertion of alkenes into a C-H bond of acetophenone.

[10] When catalyzed by palladium carboxylates, a key step is electrophilic aromatic substitution to give a Pd(II) aryl intermediate.

[12] Hydropyridination is a similar reaction, but entails addition of a pyridyl-H bond to alkenes and alkynes.