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1,4-Dehydrogenation with a Two-Coordinate Cyclic (Alkyl)(amino)silylene
Taichi Koike1, Tomoyuki Kosai1, Takeaki Iwamoto1
1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, 980-8578, Japan.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 5, 2019
Summary
Cyclic (alkyl)(amino)silylene (CAASi) 1 efficiently dehydrogenates 1,4-dihydroaromatic compounds to aromatic compounds. This reagent also activates aromatic C-H bonds, showcasing a novel reactivity for silylenes in organic synthesis.
Area of Science:
- Organometallic Chemistry
- Synthetic Organic Chemistry
Background:
- 1,4-dihydroaromatic compounds require efficient dehydrogenation methods for aromatization.
- Silylenes are reactive intermediates with diverse chemical applications.
Purpose of the Study:
- To investigate the 1,4-dehydrogenation capabilities of cyclic (alkyl)(amino)silylene (CAASi) 1.
- To explore the reactivity of CAASi 1 with various dihydroaromatic substrates.
- To elucidate the mechanism of CAASi 1-mediated dehydrogenation.
Main Methods:
- Reactions of CAASi 1 with substituted 1,4-dihydroaromatic compounds.
- Experimental studies including product isolation and characterization.
- Computational analysis to determine reaction mechanisms.
Main Results:
- CAASi 1 effectively dehydrogenates a range of 1,4-dihydroaromatic compounds.
- Unprecedented activation of aromatic C-H bonds by silylene 1 was observed with 9,10-dimethyl-9,10-dihydroanthracene, forming a silaacenaphthene derivative.
- Experimental and computational data support a stepwise hydrogen-abstraction mechanism for 1,4-dehydrogenation.
Conclusions:
- CAASi 1 is a versatile reagent for the 1,4-dehydrogenation of organic compounds.
- Silylene 1 exhibits novel reactivity, including aromatic C-H bond activation.
- The dehydrogenation mechanism primarily involves stepwise hydrogen abstraction.
Keywords:
C−H activationaromatic compoundsdehydrogenationmain-group elementsreaction mechanismssilylenesMore Related Videos
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