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Ru-catalyzed activation of free phenols in a one-step Suzuki-Miyaura cross-coupling under mechanochemical conditions.

ABSTRACT: Activation of phenols by a Ru-catalyst allows for the resulting η⁵-phenoxo complex to selectively react with a variety of nucleophiles under mechanochemical conditions. Conversion of phenolic hydroxy groups without derivatization is important for late-stage modifications of pharmaceuticals and in the context of lignin-material processing. We present a one-step, Ru-catalyzed cross-coupling of phenols with boronic acids, aryl trialkoxysilanes and potassium benzoyltrifluoroborates under mechano-chemical conditions. The protocol accepts a wide scope of starting materials and allows for gram-scale synthesis in excellent yields. The developed approach constitutes a very interesting and waste-limiting alternative to the known methods.

SUBMITTER: Mkrtchyan S

PROVIDER: S-EPMC11342143 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Ru-catalyzed activation of free phenols in a one-step Suzuki-Miyaura cross-coupling under mechanochemical conditions.

Mkrtchyan Satenik S Jakubczyk Michał M Sarfaraz Sehrish S Ayub Khurshid K Iaroshenko Viktor O VO

Chemical science 20240815

Activation of phenols by a Ru-catalyst allows for the resulting η<sup>5</sup>-phenoxo complex to selectively react with a variety of nucleophiles under mechanochemical conditions. Conversion of phenolic hydroxy groups without derivatization is important for late-stage modifications of pharmaceuticals and in the context of lignin-material processing. We present a one-step, Ru-catalyzed cross-coupling of phenols with boronic acids, aryl trialkoxysilanes and potassium benzoyltrifluoroborates under ...[more]

PMID: 39184287

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