An extension of this method to ethers was used to synthesize the natural product MKC-242, and ligands named for "John" and "Dave" are used in variations of this reaction.
An extension of this method to ethers was used to synthesize the natural product MKC-242, and ligands named for "John" and "Dave" are used in variations of this reaction. An air-stable nickel catalyst for this reaction contains tolyl, chloryl, and dppf ligands. The product distribution in this reaction is influenced by the competition between three- and four-coordinate complex intermediates, the former of which allows undesirable beta-hydride elimination. The development of this reaction was inspired by the work of Migita et al, but added an argon purge step to remove the NEt2 side product. The o-tolyl-(*) phosophine ligand used in the original version of this reaction is usually replaced with dpa, DPPF, or other bidentyl phosphines to increase rate. The second step of this reaction uses Lithium HMDS as a base under phenol reflux, which deprotonates metal-nitrogen complexes. A palladium dimer is an unusual intermediate in this reaction, and like the Stille reaction its original formulations required tin. For 10 points, name this palladium-catalyzed cross-coupling reaction between aryl halides and amines, named for two American chemists.
An extension of this method to ethers was used to synthesize the natural product MKC-242, and ligands named for "John" and "Dave" are used in variations of this reaction.
Buchwald-Hartwig reaction