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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 L.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201201244
Subject(s) - phosphine , palladium , electrophile , heteroatom , steric effects , chemistry , ligand (biochemistry) , yield (engineering) , catalysis , combinatorial chemistry , organic chemistry , ring (chemistry) , materials science , biochemistry , receptor , metallurgy
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.