期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 1, 页码 201-206出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408814
关键词
homogeneous catalysis; main group metals; hydroamination; Schwesinger base
资金
- Dutch National Research School Combination Catalysis Controlled by Chemical Design (NRSC-Catalysis)
- Humboldt foundation
Organocalcium compounds have been reported as efficient catalysts for various alkene transformations. In contrast to transition metal catalysis, the alkenes are not activated by metal-alkene orbital interactions. Instead it is proposed that alkene activation proceeds through an electrostatic interaction with a Lewis acidic Ca2+. The role of the metal was evaluated by a study using the metal-free catalysts: [Ph2N-][Me4N+] and [Ph3C-][Me4N+]. These naked amides and carbanions can act as catalysts in the conversion of activated double bonds (CO and CN) in the hydroamination of ArNCO and RNCNR (R=alkyl) by Ph2NH. For the intramolecular hydroamination of unactivated CC bonds in H2CCHCH2CPh2CH2NH2 the presence of a metal cation is crucial. A new type of hybrid catalyst consisting of a strong organic Schwesinger base and a simple metal salt can act as catalyst for the intramolecular alkene hydroamination. The influence of the cation in catalysis is further evaluated by a DFT study.
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