Homologation of Alkyl Acetates, Alkyl Ethers, Acetals, and Ketals by Formal Insertion of Diazo Compounds into a Carbon–Carbon Bond

Fei Wang; Junyi Yi; Yoshihiro Nishimoto; Makoto Yasuda

doi:10.1055/a-1523-1551

Synthesis, Table of Contents

Synthesis 2021; 53(21): 4004-4019
DOI: 10.1055/a-1523-1551

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Homologation of Alkyl Acetates, Alkyl Ethers, Acetals, and Ketals by Formal Insertion of Diazo Compounds into a Carbon–Carbon Bond

Authors

Fei Wang

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
Junyi Yi

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan
Yoshihiro Nishimoto ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^bInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan
Makoto Yasuda ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

^bInnovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan

Abstract

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Abstract

Homologation of alkyl acetates, alkyl ethers, acetals, and ketals was accomplished via formal insertion of diazo esters into carbon–carbon σ-bonds. The combined Lewis acid InI₃ with Me₃SiBr catalyzed the homologation of alkyl acetates and alkyl ethers. That of acetals and ketals was catalyzed solely by the use of InBr₃. The key point of the homologation mechanism is that the indium-based Lewis acids have the appropriate amount of Lewis acidity to achieve both the abstraction and release of leaving groups. The abstraction of a leaving group by an indium-based Lewis acid and the electrophilic addition of carbocation or oxonium intermediates to diazo esters followed by the rearrangement of carbon substituents provide the corresponding cation intermediates. Finally, the leaving group that is captured by the Lewis acid bonds with cation intermediates to furnish the homologated products.

Key words

alkyl acetates - alkyl ethers - acetals - ketals - carbocations - diazo compound - homologation - indium

Full Text

References

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Supplementary Material

Supporting Information (PDF)