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Small Substituents Make Large Differences: Aminopyrimidinyl Phosphanes Undergoing C–H Activation
Author(s) -
Farsadpour Saeid,
Ghoochany Leila Taghizadeh,
Sun Yu,
Thiel Werner R.
Publication year - 2011
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.201100659
Subject(s) - chemistry , steric effects , substituent , palladium , pyrimidine , ring (chemistry) , catalysis , electronic effect , stereochemistry , medicinal chemistry , coordination complex , organic chemistry , metal
Palladium complexes synthesised from (C 6 H 5 CN) 2 PdCl 2 and (2‐aminopyrimidinyl)phosphanes show different coordination modes depending on the nature of the amino substituent attached to the pyrimidine ring. Whereas P , N ‐coordination is observed for primary and secondary amino groups, tertiary amino groups lead to C–H activation at the pyrimidine ring. These differences result in strongly different catalytic activities in the Suzuki–Miyaura coupling reaction. The palladium complexes were characterised spectroscopically and bymeans of X‐ray structural analysis. DFT calculations were carried out to differ between the electronic and steric effects that are responsible for their behaviour in catalysis.