Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C–N Coupling
Year: 2018
Type: article
Abstract: Due to the low intrinsic acidity of amines, palladium-catalyzed C–N cross-coupling has been plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many practical obstacles associated with these reagents, we utilized a commercially available dialkyl triarylmonophosphine-supported palladium catalyst that facilitates a broad range of C–N coupling reactions in the presence of weak, soluble bases. The mild and general reaction conditions show extraordinary tolerance for even highly base-sensitive functional groups. Additionally, insightful heteronuclear NMR studies using 15 N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center.
DOI: 10.1021/jacs.8b01696
Institution: Massachusetts Institute of Technology
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G1347613584, G1947869414, Dual Catalytic Asymmetric Photoredox Coupling of alpha- Keto Radicals, G295235582, Graduate Research Fellowship Program, G5662436926, Late Transition Metal Catalysts for Organic Synthesis, G8752887869, G9000175394, G9000204311, Metal-Catalyzed Methods for Organic Synthesis
OpenAlex ID: W2789399617