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.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Angewandte Chemie International Edition
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.
Author's final manuscript