Premium
A Highly Efficient Monophosphine Ligand for Parts per Million Levels Pd‐Catalyzed Suzuki–Miyaura Coupling of (Hetero)Aryl Chlorides
Author(s) -
Choy Pui Ying,
Yuen On Ying,
Leung Man Pan,
Chow Wing Kin,
Kwong Fuk Yee
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000068
Subject(s) - chemistry , aryl , catalysis , ligand (biochemistry) , palladium , suzuki reaction , coupling reaction , medicinal chemistry , alkyl , phos , organic chemistry , combinatorial chemistry , receptor , biochemistry
A new indolylphosphine WK‐phos has been synthesized for Pd‐catalyzed Suzuki–Miyaura coupling of (hetero)aryl chlorides with (alkyl)arylboronic acids. Comprising this newly developed ligand with palladium(II) acetate, the resulting catalyst system was found to be highly effective in facilitating the reaction even when the catalyst loading reaches parts per million levels (e.g. 10 ppm). These examples represent one of the lowest catalyst loadings reported to date of employing monophosphine (e.g. Ar‐PCy 2 ) for Suzuki–Miyaura reactions. The ligand geometry has also been well‐characterized by single‐crystal X‐ray crystallography.