A Bulky Biaryl Phosphine Ligand Allows for Palladium-Catalyzed Amidation of Five-Membered Heterocycles as Electrophiles
Author(s)
Su, Mingjuan; Buchwald, Stephen Leffler
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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.
Date issued
2012-03Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
ISSN
14337851
1521-3773