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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Multicomponent reactions of convertible isonitriles
Michael C Pirrung1, Subir Ghorai, Tannya R Ibarra-Rivera
1Department of Chemistry, University of California, Riverside, California 92521-0403, USA. michael.pirrung@ucr.edu
The Journal of Organic Chemistry
|May 5, 2009
Summary
New unsaturated isonitriles derived from oxazoles offer a safer, more versatile alternative for organic synthesis. These compounds are odor-free and facilitate easy separation of products using fluorous solid-phase extraction.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Isonitriles are valuable synthetic reagents but are often associated with unpleasant odors and limited reactivity.
- Conventional methods for isonitrile synthesis, such as formamide dehydration, have drawbacks.
Purpose of the Study:
- To develop a novel and accessible family of unsaturated isonitriles.
- To explore their utility in multicomponent reactions and subsequent transformations.
- To investigate the application of perfluorinated isonitriles in fluorous solid-phase extraction.
Main Methods:
- Base-promoted ring-opening of oxazoles to generate unsaturated isonitriles.
- Utilizing these isonitriles in various multicomponent reactions.
- Employing fluorous solid-phase extraction for product separation with perfluorinated isonitriles.
Main Results:
- A new class of unsaturated isonitriles was successfully synthesized.
- These isonitriles participate in standard isonitrile multicomponent reactions, yielding convertible amide products.
- Perfluorinated isonitriles enabled efficient separation of reagents and products via fluorous solid-phase extraction.
- The synthesized isonitriles lack the characteristic pungent odor of traditional isonitriles.
Conclusions:
- The base-promoted ring-opening of oxazoles provides an effective alternative route to unsaturated isonitriles.
- These novel isonitriles are versatile reagents for organic synthesis, offering improved handling and reactivity.
- The development of odor-free and easily separable isonitriles expands their applicability in synthetic chemistry.
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