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N‐Heterocyclic Olefin‐Ligated Palladium(II) Complexes as Pre‐Catalysts for Buchwald–Hartwig Aminations
Author(s) -
Watson Ian C.,
Schumann André,
Yu Haoyang,
Davy Emma C.,
McDonald Robert,
Ferguson Michael J.,
HeringJunghans Christian,
Rivard Eric
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901376
Subject(s) - palladium , chemistry , carbene , catalysis , olefin fiber , ligand (biochemistry) , combinatorial chemistry , polymer chemistry , medicinal chemistry , organic chemistry , biochemistry , receptor
New N‐heterocyclic olefins (NHOs) are described with functionalization on the ligand heterocyclic backbone and terminal alkylidene positions. Various Pd II –NHO complexes have been formed and their use as pre‐catalysts in Buchwald–Hartwig aminations was explored. The most active system for catalytic C−N bond formation between hindered arylamine and arylhalide substrates was accessed by combining a backbone methylated NHO with [Pd(cinnamyl)Cl] 2 in the presence of NaO t Bu as a base. In these active systems evidence suggests that catalysis is mediated by colloidal palladium metal, highlighting a different coordination ability of NHOs in comparison with commonly used N‐heterocyclic carbene co‐ligands.