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Synlett 2024; 35(04): 367-378
DOI: 10.1055/a-2136-3609
DOI: 10.1055/a-2136-3609
account
11th Singapore International Chemistry Conference (SICC-11)
Acetate/Alkoxide/Halide Shuttle Systems Mediated by Lewis Acid Catalysts for Insertion Reaction of a One-Carbon Unit into Carbon–Carbon or Carbon–Halogen Bonds
This work was supported by the Core Research for Evolutional Science and Technology, Core Research for Evolutional Science and Technology (JST CREST; Grant Number JPMJCR20R3), Japan, and a Grant-in-Aid for Transformative Research Areas (A) (21H05212) Digitalization-driven Transformative Organic Synthesis (Digi-TOS) from the Ministry of Education, Culture, Sports, Science & Technology, Japan. It was also supported by Japan Society for the Promotion of Science (JSPS) KAKENHI (grant number JP19K05455).
Abstract
In this account, we describe our research on a Lewis acid-catalyzed insertion reaction of α-diazo esters into a carbon–carbon or carbon–halogen bond. Indium catalysts mediated not only the insertion of α-diazo esters into a carbon–carbon bond of alkyl acetates, alkyl ethers, acetals, and alkyl halides, but also a carbon–halogen bond of alkyl chlorides, bromides, and iodides. BF3 specifically accelerated the insertion of α-diazo esters into a carbon–fluorine bond. The key to this catalysis is acetate, alkoxide, and halide shuttle systems mediated by a Lewis acid, in which the Lewis acid abstracts a leaving group from a starting substrate and releases the leaving group to the appropriate carbocation intermediate in the catalytic cycle.
1 Introduction
2 Acetate/Alkoxide Shuttle: Insertion Reaction of α-Diazo Esters into a Carbon–Carbon Bond of Alkyl Acetates, Alkyl Ethers, and Acetals
3 Halide Shuttle: Insertion Reaction of α-Diazo Esters into a Carbon–Carbon Bond of Alkyl Halides
4 Halide Shuttle: Insertion of α-Diazo Esters into a Carbon–Halogen Bond of Alkyl Halides
5 Conclusion
Key words
insertion reactions - C–C bonds - C–halogen bonds - diazo compounds - Lewis acids - alkyl acetates - alkyl ethers - acetals - alkyl halidesPublikationsverlauf
Eingereicht: 30. April 2023
Angenommen nach Revision: 24. Juli 2023
Accepted Manuscript online:
24. Juli 2023
Artikel online veröffentlicht:
11. September 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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Pioneering works:
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For selected reviews on C–F transformation, see:
For the insertion reaction of a carbon unit into a C–F bond, see:
For selected papers on fluoride abstraction by aluminum Lewis acids, see:
For selected recent papers, see:
For selected recent papers, see:
Selected recent papers: