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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Enantioselective iridium-catalyzed allylic arylation
Damien Polet1, Xavier Rathgeb, Caroline A Falciola
1Department of Organic Chemistry, University of Geneva, 30 quai Ernest Ansermet, 1211 Genève 4, Switzerland.
This study introduces the first iridium-catalyzed allylic substitution using arylzinc reagents, achieving high enantioselectivity. The method is versatile, enabling the synthesis of complex molecules like (+)-sertraline.
Area of Science:
- Organometallic Chemistry
- Asymmetric Catalysis
Background:
- Allylic substitution reactions are fundamental in organic synthesis.
- Developing enantioselective methods for C-C bond formation is crucial.
Purpose of the Study:
- To develop the first iridium-catalyzed allylic substitution employing arylzinc nucleophiles.
- To achieve high enantioselectivity in these transformations.
Main Methods:
- Utilized iridium catalysts for allylic substitution reactions.
- Employed arylzinc nucleophiles derived from Grignard reagents.
- Investigated compatibility with halogen/metal exchange reactions.
Main Results:
- Achieved high enantioselectivities in the iridium-catalyzed allylic substitution.
- Demonstrated the utility of Grignard reagents as starting materials.
- Confirmed compatibility with halogen/metal exchange processes.
Conclusions:
- Established a novel and efficient iridium-catalyzed allylic substitution methodology.
- Showcased the synthetic applicability through the formal synthesis of (+)-sertraline.
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