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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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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.
Date issued
2012-03
URI
http://hdl.handle.net/1721.1/81944
Department
Massachusetts Institute of Technology. Department of Chemistry
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
ISSN
14337851
1521-3773

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