Abstract
An in situ generated Pd–Cy*Phine catalyst has been successfully applied to the N-arylation of primary and secondary amines, and it exhibited high performance across multiple substrate classes. The performance induced by the meta-terarylphosphine motif of the Cy*Phine ligand for C−N cross-coupling displayed only subtle differences to that of its biarylphosphine congener XPhos. DFT studies demonstrated comparable reaction energetics in the catalytic cycle steps for both Pd–Cy*Phine and Pd–XPhos, which was consistent with previous findings. The computational investigation also indicated that a putative rate-determining step occurred after amine binding, which was likely to have annulled the expected benefits of having a meta-terarylphosphine ligand architecture.
Original language | English |
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Pages (from-to) | 750-757 |
Number of pages | 8 |
Journal | ChemPlusChem |
Volume | 82 |
Issue number | 5 |
DOIs | |
Publication status | Published or Issued - 1 May 2017 |
Externally published | Yes |
Keywords
- amines
- arylation
- cross-coupling
- homogeneous catalysis
- palladium
ASJC Scopus subject areas
- General Chemistry