Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C–N Coupling
Author(s)
Dennis, Joseph M.; White, Nicholas A.; Liu, Richard; Buchwald, Stephen Leffler
DownloadAccepted version (961.3Kb)
Terms of use
Metadata
Show full item recordAbstract
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.
Date issued
2018-03Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Dennis, Joseph M. et al. "Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C–N Coupling." Journal of the American Chemical Society 140, 13 (March 2018): 4721–4725 © 2018 American Chemical Society
Version: Author's final manuscript
ISSN
0002-7863
1520-5126