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

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...

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Published inSynthesis (Stuttgart) Vol. 53; no. 17; pp. 3037 - 3044
Main Authors Shimazumi, Ryoma, Morita, Kosuke, Yoshida, Tomoki, Yasui, Kosuke, Tobisu, Mamoru
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.09.2021
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cross-coupling
nickel
late-stage functionalization
C-O bond activation
natural product
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1467-2494