期刊
DALTON TRANSACTIONS
卷 49, 期 29, 页码 10114-10119出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0dt00786b
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资金
- Vanderbilt University
- National Science Foundation [CHE-1847813]
- American Chemical Society Petroleum Research Fund
Nucleophilic aromatic substitution (SNAr) of fluorobenzene by morpholine at a bis(diphenylphosphino)pentane-supported ruthenim complex is investigated as a model system for pi-arene catalysis through the synthesis and full characterization of proposed intermediates. The SNAr step proceeds quickly at room temperature, however the productN-phenylmorpholine binds tightly to the ruthenium ion. In the case examined, the thermodynamics of arene binding favor productN-phenylmorpholine over fluorobenzene binding by a factor of 2000, corresponding to significant product inhibition. Observations of the catalyst resting state support this hypothesis and demonstrate an additive-controlled role for a previously-proposed ligand cyclometalation.
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