Empirical and Computational Insights into N-Arylation Reactions Catalyzed by Palladium meta -Terarylphosphine Catalyst
| Autor: | Yee Hwee Lim, Michael B. Sullivan, Fui Fong Yong, Edward G. Robins, Adrian M. Mak, Howard Jong, Charles W. Johannes, Wenqin Wu |
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| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Chemistry Ligand Substrate (chemistry) Amine binding chemistry.chemical_element Homogeneous catalysis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Catalytic cycle XPhos Palladium |
| Zdroj: | ChemPlusChem. 82:750-757 |
| ISSN: | 2192-6506 |
| DOI: | 10.1002/cplu.201700042 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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