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Updated: Jun 21, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
A straightforward protocol for one-pot allylic aminations/Stille couplings
Christian Bukovec1, Uli Kazmaier
1Universität des Saarlandes, Institut für Organische Chemie, Im Stadtwald, Geb. C4.2, D-66123 Saarbrücken, Germany.
Organic Letters
|July 9, 2009
Summary
Stannylated allylic carbonates enable efficient palladium-catalyzed allylic aminations. The resulting amines can be coupled with electrophiles via the Stille protocol, yielding complex molecules.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Palladium-catalyzed allylic amination is a key transformation in organic synthesis.
- Developing efficient methods for constructing highly functionalized molecules is crucial.
Purpose of the Study:
- To investigate the utility of stannylated allylic carbonates as substrates for palladium-catalyzed allylic amination.
- To explore the direct coupling of in-situ generated stannylated allylic amines with electrophiles.
Main Methods:
- Utilizing stannylated allylic carbonates in palladium-catalyzed reactions.
- Employing [Pd(allyl)Cl](2) as a catalyst in N,N-Dimethylformamide (DMF).
- Applying the Stille coupling protocol for subsequent functionalization.
Main Results:
- Stannylated allylic carbonates serve as effective substrates for Pd-catalyzed allylic amination.
- The stannylated allylic amines formed can be directly coupled with various electrophiles.
- This methodology provides highly functionalized building blocks in excellent yields.
Conclusions:
- This study demonstrates a novel and efficient route to complex organic molecules.
- The combined Pd-catalyzed amination and Stille coupling offers a powerful synthetic strategy.
- The method is valuable for accessing diverse and highly functionalized building blocks.
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