Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C–N Coupling
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nihms950850.pdf
Description
Accepted version
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961.38 KB
Format
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Checksum (MD5)
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Author(s)
Dennis, Joseph M.
White, Nicholas A.
Liu, Richard
Buchwald, Stephen Leffler
Date Issued
March 2018
Journal
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/jacs.8b01696
