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Resorcinarenyl‐Phosphines in Suzuki–Miyaura Cross‐Coupling Reactions of Aryl Chlorides
Author(s) -
Monnereau Laure,
El Moll Hani,
Sémeril David,
Matt Dominique,
Toupet Loïc
Publication year - 2014
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201301473
Subject(s) - phosphine , aryl , halide , chemistry , oxidative addition , ligand (biochemistry) , catalysis , metal , coupling reaction , combinatorial chemistry , medicinal chemistry , organic chemistry , polymer chemistry , alkyl , biochemistry , receptor
Two phosphines built on a bowl‐shaped resorcin[4]arene skeleton, namely 5‐diphenylphosphanyl‐ and 5‐diisopropylphosphanyl‐4(24),6(10),12(16),18(22)‐tetramethylenedioxy‐2,8,14,20‐tetrapentylresorcin[4]arene, have been synthesised and tested in the Suzuki–Miyaura cross‐coupling reaction of aryl halides. Combining these ligands with [Pd(OAc) 2 ] resulted in highly active catalysts that allowed the formation of o , o ′‐biphenyls starting from aryl chlorides. The remarkable activities observed possibly arise from 1) the capacity of the phosphines to operate transiently as P , O chelators, thereby increasing the electron density of the metal, and 2) the ability of the ligands to embed metal–organic units, which, when occurring, makes the ligand considerably bulkier so as to disfavour the coordination of a second phosphine. Both features are known to facilitate the oxidative addition step.