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Application of aryloximes as solid-phase ketone linkers.
Salvatore D Lepore1, Michael R Wiley
1Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN 46285, USA. slepore@fau.edu
Organic Letters
|January 3, 2003
Summary
Ketone oxime anions react with fluorobenzonitriles to form aryloxime adducts. These adducts cyclize to ketones, with solid-phase synthesis enabling efficient ketone production via coupling and cyclorelease.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Nucleophilic aromatic substitution (SNAr) is a key reaction in organic synthesis.
- Ketone synthesis often involves multi-step processes.
Purpose of the Study:
- To develop a novel synthetic route for ketone production.
- To explore the application of ketone oxime anions in SNAr reactions.
- To investigate solid-phase synthesis for efficient ketone generation.
Main Methods:
- Treatment of ketone oxime anions with 4-substituted-2-fluorobenzonitriles in solution and on solid phase.
- Acid-catalyzed cyclization of aryloxime adducts.
- Suzuki and amide coupling reactions on resin-bound oximes followed by cyclorelease.
Main Results:
- Formation of nucleophilic aromatic substitution aryloxime adducts.
- Successful cyclization of adducts to ketones under aqueous acidic conditions.
- Good yields and purities of ketone products from solid-phase synthesis.
Conclusions:
- A versatile method for ketone synthesis using ketone oxime anions and fluorobenzonitriles has been established.
- Solid-phase synthesis offers an efficient and high-yielding approach for ketone production.