Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C–N Coupling
Department of Chemistry, Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States
J. Am. Chem. Soc., 2018, 140 (13), pp 4721–4725
DOI: 10.1021/jacs.8b01696
Publication Date (Web): March 12, 2018
Copyright © 2018 American Chemical Society
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 15N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center.
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b01696.
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