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06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
N-acylsulfonamide linker activation by Pd-catalyzed allylation
Yi He1, Jesse P Wilkins, Laura L Kiessling
1Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Organic Letters
|June 2, 2006
Summary
N-acylsulfonamide linkers are activated using mild palladium conditions for efficient synthesis. This novel method enhances the utility of these stable linkers in solid-phase organic synthesis, particularly for thioester preparation.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- N-acylsulfonamide linkers offer stability in solid-phase synthesis but require activation for compound cleavage.
- Existing activation methods can be harsh or limited in scope.
Purpose of the Study:
- To develop a mild and efficient method for activating N-acylsulfonamide safety-catch linkers.
- To demonstrate the utility of this new activation strategy in organic synthesis.
Main Methods:
- Reaction of the N-acylsulfonamide group with a pi-allyl palladium complex under neutral conditions.
- Application of the activated linker in the synthesis of thioesters.
Main Results:
- Successful activation of the N-acylsulfonamide linker using palladium catalysis.
- Efficient synthesis of thioesters was achieved utilizing the novel activation method.
Conclusions:
- Palladium-catalyzed activation provides a mild and effective route for N-acylsulfonamide linker cleavage.
- This approach broadens the applicability of N-acylsulfonamide linkers in complex molecule synthesis.
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