Synlett 2024; 35(04): 367-378
DOI: 10.1055/a-2136-3609
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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

a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan
,
Makoto Yasuda
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
b   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan
› Author Affiliations
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



Publication History

Received: 30 April 2023

Accepted after revision: 24 July 2023

Accepted Manuscript online:
24 July 2023

Article published online:
11 September 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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