A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles
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Buchwald_A bulky biaryl.pdf
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1.97 MB
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Author(s)
Su, Mingjuan
Buchwald, Stephen Leffler
Date Issued
March 2012
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Su, Mingjuan, and Stephen L. Buchwald. “A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles.” Angewandte Chemie International Edition 51, no. 19 (May 7, 2012): 4710-4713.
Version
Author's final manuscript
Abstract
The incredible bulk: The first palladium-catalyzed amidation of five-membered heterocyclic bromides with multiple heteroatoms was achieved using the Pd/1 catalyst system. N-Arylated imidazoles, pyrazoles, thiazoles, pyrroles, and thiophenes were synthesized in moderate to excellent yield. Experimental results and DFT calculations point to the need for an electron-rich and sterically demanding biaryl phosphine ligand to promote these difficult reactions.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike 3.0
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DOI of Published Version
https://doi.org/10.1002/anie.201201244
