Abstract
Cyclic (alkyl)(amino)silylene (CAASi) 1 has been found to successfully dehydrogenate 1,4-dihydroaromatic compounds containing various substituents to afford the corresponding aromatic compounds. The observed high substrate generality proves 1 to be a potential 1,4-dehydrogenation reagent for organic compounds. For the reaction with 9,10-dimethyl-9,10-dihydroanthracene, silylene 1 activated not only benzylic C−H bonds but also aromatic C−H bonds to yield a silaacenaphthene derivative, which is an unprecedented reaction of silylenes. The results of the experimental and computational study of the reaction of CAASi 1 with 9,10-dihydroanthracene and 1,4-cyclohexadiene are consistent with the notion that 1,4-dehydrogenation with CAASi 1 proceeds mainly through a stepwise hydrogen-abstraction mechanism.
Original language | English |
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Pages (from-to) | 9295-9302 |
Number of pages | 8 |
Journal | Chemistry - A European Journal |
Volume | 25 |
Issue number | 39 |
DOIs | |
Publication status | Published - 2019 Jul 11 |
Keywords
- C−H activation
- aromatic compounds
- dehydrogenation
- main-group elements
- reaction mechanisms
- silylenes
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry