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.
By using mechanistic insight, a new ligand (EPhos) for the n class="Chemical">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.
Authors: Alexander Buitrago Santanilla; Erik L Regalado; Tony Pereira; Michael Shevlin; Kevin Bateman; Louis-Charles Campeau; Jonathan Schneeweis; Simon Berritt; Zhi-Cai Shi; Philippe Nantermet; Yong Liu; Roy Helmy; Christopher J Welch; Petr Vachal; Ian W Davies; Tim Cernak; Spencer D Dreher Journal: Science Date: 2014-11-20 Impact factor: 47.728
Authors: Gen Li; Trevor V Nykaza; Julian C Cooper; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich Journal: J Am Chem Soc Date: 2020-03-25 Impact factor: 15.419