CH 24 - Catalytic C=C bond - Organometallic Chemistry Pt2

organopalladium chemistry

important reactions of transition metals and transition metal compounds

oxidative addition

addition of a reagent to a metal center causing it to add two substituents and to increase its oxidation state by two

• can occur with a metal coordinated with one or more ligands (Ln) or with a free metal, M(0)

reductive elimination

elimination of two substituents at a metal center, causing the oxidation state of the metal to decrease by two

sonogashira cross-coupling steps

1. CuI/NEt3 - adds Cu to end

2. R-I and Pd cat. (R replaces Cu)

sonogashira cross-coupling can be done twice with

one end of acetylene protected

• add protecting group and then remove with Bu4N+F-

sonogashira cross-coupling catalytic in

Pd and can be preformed even without Cu

suzuki cross-coupling

• addition reaction

• reagent contains borane

stille cross-coupling

• addition reaction

  • reagent has n-Bu3Sn-R

organopalladium chemistry mechanism

1. oxidative addition

2. transmetallation

3. reductive elimination