ABSTRACT
Organolithium, Grignard, and Gilman reagents are mainstays of organic chemistry, but they have several drawbacks. First, all three are stoichiometric reagents, which means that the metal must be used in a full equivalent with the starting haloalkanes. Second, the high reactivity of these reagents means that they are not particularly selective. By switching to another metal, palladium, we can correct both of these shortcomings. This chapter investigates palladium cross-coupling chemistry, which introduces students to modern, widely used organic reactions. Palladium cross-coupling reactions are also one of the premier ways to synthesize carbon-carbon bonds. A mechanistic understanding of the three steps of cross-coupling (oxidative addition, transmetalation, and reductive elimination) is provided along with examples of the breadth of potential cross-coupling partners
