Late-Stage Derivatization of Buflavine by Nickel-Catalyzed Direct Substitution of a Methoxy Group via C–O Bond Activation

Ryoma Shimazumi; Kosuke Morita; Tomoki Yoshida; Kosuke Yasui; Mamoru Tobisu

doi:10.1055/a-1467-2494

Synthesis, Table of Contents

Synthesis 2021; 53(17): 3037-3044
DOI: 10.1055/a-1467-2494

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Late-Stage Derivatization of Buflavine by Nickel-Catalyzed Direct Substitution of a Methoxy Group via C–O Bond Activation

Ryoma Shimazumi

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

,

Kosuke Morita

^bNada High School, Kobe, Hyogo 658-0082, Japan

,

Tomoki Yoshida

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

,

Kosuke Yasui

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

,

Mamoru Tobisu ∗

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

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

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Abstract

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Dedicated to Professor Shinji Murai for his contribution to bond activation.

Abstract

The nickel-catalyzed cross-coupling of methoxyarenes was applied to buflavine, which allows for the selective monosubstitution of one of the two methoxy groups in the molecule, leading to the formation of 2- and 3-substituted isomers. Trimethylsilylmethyl (TMSCH₂), phenyl, and alkynyl groups can be introduced into buflavine using this method. The resulting TMSCH₂ analogue of buflavine can also be converted into several other derivatives.

Key words

C–O bond activation - cross-coupling - nickel - natural product - late-stage functionalization

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References

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Supporting Information