Overall Score4.5
- Generality
- Reagent Availability
- Experimental User Friendliness
- Safety and Environmental Impact
- Criteria #5
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General Characteristics
TMPMgCl-LiCl is known as the Knochel-Hauser base and a useful reagent for directed metalation of aromatic compounds.
The metalation of aromatic compounds are conventionally done by using alkyllithiums and lithium amides, but these bases are often accompanied with side reactions due to their high nuclephilicity.
In contrast, TMPMgCl-LiCl has higher functional group tolerance and can be used at a practical temperature range. This reagent can be used for otherwise-difficult metalation of electron-poor heteroaromatic rings.
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General References
Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 2958. DOI: 10.1002/anie.200504024
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Reaction Mechanism
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Examples
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Experimental Procedure
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Experimental Tips
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References
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