Journal
REACTION CHEMISTRY & ENGINEERING
Volume 6, Issue 7, Pages 1212-1219Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1re00124h
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Funding
- Natural Sciences and Engineering Research Council
- GlaxoSmithKline
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A specific combination of catalyst, solvent, base, and additives was crucial for both activity and selectivity in the Mizoroki-Heck arylation of electron-rich alkenes. This was especially important when translating screening hits into preparative-scale synthesis.
The Mizoroki-Heck arylation of electron-rich alkenes such as butyl vinyl ether often results in regioisomeric mixtures of products under typical reaction conditions. To discover new catalytic systems for achieving alpha-selective arylation, an alternative approach to generating aryl methyl ketones, we have combined microscale high-throughput experimentation with mechanistic studies on a model system. A specific combination of catalyst, solvent, base, and additives was found to be crucial for both activity and selectivity, especially when translating screening hits into preparative-scale synthesis.
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