Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling was written by Dennis, Joseph M.;White, Nicholas A.;Liu, Richard Y.;Buchwald, Stephen L.. And the article was included in Journal of the American Chemical Society in 2018.COA of Formula: C7H8BrNO2 This article mentions the following:
Using the dimeric palladium complex of an electron-deficient terarylphosphine as catalyst, aryl bromides and triflates and an aryl chloride underwent chemoselective Buchwald-Hartwig amination reactions with primary amines, amides, and aryl amines mediated by the soluble base DBU to yield arylamines; base-sensitive functional groups such as β-haloethyl ethers were tolerated in the amination. Determination of the 31P-15N coupling constants of arylphosphine palladium [15N]amine complexes and calculations of their HOMO-LUMO gaps and at. charges on Pd indicated that the more hindered adamantyl-substituted ligands lead to lower electron densities at Pd and thus more easily deprotonated coordinated amines. In the experiment, the researchers used many compounds, for example, Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3COA of Formula: C7H8BrNO2).
Methyl 4-bromo-1-methyl-1H-pyrrole-2-carboxylate (cas: 1196-90-3) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. The principal reactions for organobromides include dehydrobromination, Grignard reactions, reductive coupling, and nucleophilic substitution.COA of Formula: C7H8BrNO2
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary