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Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities

[Image: see text] 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 CF(3)-tertiary alcohols in moderate to excellent yields (up to 95% yield) with good tolerance...

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Autores principales: Zhou, Bingyi, Yang, Guoyu, Wang, Caixia, Liu, Lijie, Shi, Lijun, Pan, Zhenliang, Ji, Xiaoming, Wu, Lulu, Zheng, Huayu, Xu, Cuilian, Fan, Liangxin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609063/
https://www.ncbi.nlm.nih.gov/pubmed/36312435
http://dx.doi.org/10.1021/acsomega.2c05855
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author Zhou, Bingyi
Yang, Guoyu
Wang, Caixia
Liu, Lijie
Shi, Lijun
Pan, Zhenliang
Ji, Xiaoming
Wu, Lulu
Zheng, Huayu
Xu, Cuilian
Fan, Liangxin
author_facet Zhou, Bingyi
Yang, Guoyu
Wang, Caixia
Liu, Lijie
Shi, Lijun
Pan, Zhenliang
Ji, Xiaoming
Wu, Lulu
Zheng, Huayu
Xu, Cuilian
Fan, Liangxin
author_sort Zhou, Bingyi
collection PubMed
description [Image: see text] 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 CF(3)-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 EC(50) value of 0.18 mg/mL.
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spelling pubmed-96090632022-10-28 Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities Zhou, Bingyi Yang, Guoyu Wang, Caixia Liu, Lijie Shi, Lijun Pan, Zhenliang Ji, Xiaoming Wu, Lulu Zheng, Huayu Xu, Cuilian Fan, Liangxin ACS Omega [Image: see text] 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 CF(3)-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 EC(50) value of 0.18 mg/mL. American Chemical Society 2022-10-10 /pmc/articles/PMC9609063/ /pubmed/36312435 http://dx.doi.org/10.1021/acsomega.2c05855 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Zhou, Bingyi
Yang, Guoyu
Wang, Caixia
Liu, Lijie
Shi, Lijun
Pan, Zhenliang
Ji, Xiaoming
Wu, Lulu
Zheng, Huayu
Xu, Cuilian
Fan, Liangxin
Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities
title Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities
title_full Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities
title_fullStr Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities
title_full_unstemmed Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities
title_short Highly Chemoselective Synthesis of Azaarene-Equipped CF(3)-Tertiary Alcohols under Metal-Free Conditions and Their Fungicidal Activities
title_sort highly chemoselective synthesis of azaarene-equipped cf(3)-tertiary alcohols under metal-free conditions and their fungicidal activities
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609063/
https://www.ncbi.nlm.nih.gov/pubmed/36312435
http://dx.doi.org/10.1021/acsomega.2c05855
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