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Mechanistic Insight Leads to a Ligand Which Facilitates the Palladium‐Catalyzed Formation of 2‐(Hetero)Arylaminooxazoles and 4‐(Hetero)Arylaminothiazoles
Author(s) -
Olsen Esben P. K.,
Arrechea Pedro L.,
Buchwald Stephen L.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705525
Subject(s) - palladium , catalysis , ligand (biochemistry) , chemistry , aryl , halide , reactivity (psychology) , combinatorial chemistry , homogeneous , homogeneous catalysis , organic chemistry , medicine , biochemistry , alkyl , receptor , alternative medicine , thermodynamics , physics , pathology
By using mechanistic insight, a new ligand (EPhos) for the palladium‐catalyzed C−N cross‐coupling between primary amines and aryl halides has been developed. Employing an isopropoxy group at the C3‐position favors the C‐bound isomer of the ligand‐supported palladium(II) complexes and leads to significantly improved reactivity. The use of a catalyst system based on EPhos with NaOPh as a mild homogeneous base proved to be very effective in the formation of 4‐arylaminothiazoles and highly functionalized 2‐arylaminooxazoles. Previously, these were not readily accessible using palladium catalysis.