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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
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Kosuke Morita
b   Nada High School, Kobe, Hyogo 658-0082, Japan
,
Tomoki Yoshida
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Kosuke Yasui
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
,
Mamoru Tobisu  ∗
a   Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
c   Innovative Catalysis Science Division, Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan
› Author AffiliationsThis work was supported, in part, by the SEEDS program from Osaka University.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1467-2494.
  • Supporting Information


Publication History

Received: 10 March 2021

Accepted after revision: 25 March 2021

Accepted Manuscript online:
25 March 2021

Article published online:
21 April 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
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