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Highly Chemoselective Synthesis of Azaarene-Equipped CF₃-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities.

ABSTRACT: A highly chemoselective reaction between α,β-unsaturated trifluoromethyl ketones with azaarenes under metal-free conditions was carried out, affording a range of valuable azaarene-equipped CF₃-tertiary alcohols in moderate to excellent yields (up to 95% yield) with good tolerance of functional groups, and their structures were confirmed by NMR, HRMS, and X-ray diffraction for validation. This method features simple reaction conditions (only solvent), high atom- and step-economy, and broad substrate scope. Moreover, most of the target products exhibited promising fungicidal activities, and compound 3al exhibited 91.65% fungicidal activity against R. solani, with an EC₅₀ value of 0.18 mg/mL.

SUBMITTER: Zhou B

PROVIDER: S-EPMC9609063 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

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Highly Chemoselective Synthesis of Azaarene-Equipped CF3-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities.

Zhou Bingyi B Yang Guoyu G Wang Caixia C Liu Lijie L Shi Lijun L Pan Zhenliang Z Ji Xiaoming X Wu Lulu L Zheng Huayu H Xu Cuilian C Fan Liangxin L

ACS omega 20221010 42

A highly chemoselective reaction between α,β-unsaturated trifluoromethyl ketones with azaarenes under metal-free conditions was carried out, affording a range of valuable azaarene-equipped CF3-tertiary alcohols in moderate to excellent yields (up to 95% yield) with good tolerance of functional groups, and their structures were confirmed by NMR, HRMS, and X-ray diffraction for validation. This method features simple reaction conditions (only solvent), high atom- and step-economy, and b ...[more]

PMID: 36312435

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