title: Aqueous Suzuki Coupling Reactions of Basic Nitrogen-Containing Substrates in the Absence of Added Base and Ligand: Observation of High Yields under Acidic Conditions.
abstract: A series of aqueous heterogeneous Suzuki coupling reactions of substrates containing basic nitrogen centers with phenylboronic acid in the absence of added base and ligand is presented. High yields of products were obtained by employing aryl bromides containing aliphatic 1°, 2°, and 3° amine substituents, and good to high yields were obtained by employing a variety of substituted bromopyridines. In the former series, the pH of the aqueous phase changed from basic to acidic during the course of the reaction, while in the latter series the aqueous phase was on the acidic side of the pH scale throughout the entire course of reaction. A mechanistic interpretation for these observations, which generally preserves the oxo palladium catalytic cycle widely accepted in the literature, is presented.
authors: School of Chemistry and Biochemistry, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.
authors: Zhao
authors: Z
authors: Li
authors: School of Chemistry and Biochemistry, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.
authors: Carol
authors: C
authors: Gelbaum
authors: The Dow Chemical Company, Midland, Michigan 48674, United States.
authors: Jason S
authors: JS
authors: Fisk
authors: The Dow Chemical Company, Midland, Michigan 48674, United States.
authors: Bruce
authors: B
authors: Holden
authors: The Dow Chemical Company, Midland, Michigan 48674, United States.
authors: Arvind
authors: A
authors: Jaganathan
authors: Dow AgroSciences, Indianapolis, Indiana 46268, United States.
authors: Gregory T
authors: GT
authors: Whiteker
authors: School of Chemistry and Biochemistry, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.
authors: Pamela
authors: P
authors: Pollet
authors: School of Chemistry and Biochemistry, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.|School of Chemical and Biomolecular Engineering, Georgia Institute of Technology , Atlanta, Georgia 30332, United States.
authors: Charles L
authors: CL
authors: Liotta