Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition
Summary: Aryl halide (Br, Cl, I) is among the most important compounds in pharmaceutical industry, material science, and agrochemistry, broadly utilized in diverse transformations. Tremendous approaches have been established to prepare this scaffold; however, many of them suffer from atom economy, h...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-05-01
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| Series: | iScience |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004220302571 |
| _version_ | 1828888904346894336 |
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| author | Zhuang Ma Helin Lu Ke Liao Zhilong Chen |
| author_facet | Zhuang Ma Helin Lu Ke Liao Zhilong Chen |
| author_sort | Zhuang Ma |
| collection | DOAJ |
| description | Summary: Aryl halide (Br, Cl, I) is among the most important compounds in pharmaceutical industry, material science, and agrochemistry, broadly utilized in diverse transformations. Tremendous approaches have been established to prepare this scaffold; however, many of them suffer from atom economy, harsh condition, inability to be scaled up, or cost-unfriendly reagents and catalysts. Inspired by vanadium haloperoxidases herein we presented a biomimetic approach for halogenation (Br, Cl, I) of (hetero)arene catalyzed by tungstate under mild pH in a cost-efficient and environment- and operation-friendly manner. Broad substrates, diverse functional group tolerance, and good chemo- and regioselectivities were observed, even in late-stage halogenation of complex molecules. Moreover, this approach can be scaled up to over 100 g without time-consuming and costly column purification. Several drugs and key precursors for drugs bearing aryl halides (Br, Cl, I) have been conveniently prepared based on our approach. |
| first_indexed | 2024-12-13T12:31:58Z |
| format | Article |
| id | doaj.art-f06a3252c88f4e3bbf684e1b1f3fbcd3 |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-12-13T12:31:58Z |
| publishDate | 2020-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-f06a3252c88f4e3bbf684e1b1f3fbcd32022-12-21T23:46:01ZengElsevieriScience2589-00422020-05-01235Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild ConditionZhuang Ma0Helin Lu1Ke Liao2Zhilong Chen3School of Pharmacy, Tongji Medical School, Huazhong University of Science and Technology (HUST), 13# Hang Kong Road, Qiaokou District, Wuhan, Hubei 430030, P. R. ChinaSchool of Pharmacy, Tongji Medical School, Huazhong University of Science and Technology (HUST), 13# Hang Kong Road, Qiaokou District, Wuhan, Hubei 430030, P. R. ChinaSchool of Pharmacy, Tongji Medical School, Huazhong University of Science and Technology (HUST), 13# Hang Kong Road, Qiaokou District, Wuhan, Hubei 430030, P. R. ChinaSchool of Pharmacy, Tongji Medical School, Huazhong University of Science and Technology (HUST), 13# Hang Kong Road, Qiaokou District, Wuhan, Hubei 430030, P. R. China; Corresponding authorSummary: Aryl halide (Br, Cl, I) is among the most important compounds in pharmaceutical industry, material science, and agrochemistry, broadly utilized in diverse transformations. Tremendous approaches have been established to prepare this scaffold; however, many of them suffer from atom economy, harsh condition, inability to be scaled up, or cost-unfriendly reagents and catalysts. Inspired by vanadium haloperoxidases herein we presented a biomimetic approach for halogenation (Br, Cl, I) of (hetero)arene catalyzed by tungstate under mild pH in a cost-efficient and environment- and operation-friendly manner. Broad substrates, diverse functional group tolerance, and good chemo- and regioselectivities were observed, even in late-stage halogenation of complex molecules. Moreover, this approach can be scaled up to over 100 g without time-consuming and costly column purification. Several drugs and key precursors for drugs bearing aryl halides (Br, Cl, I) have been conveniently prepared based on our approach.http://www.sciencedirect.com/science/article/pii/S2589004220302571Pharmaceutical EngineeringOrganic ChemistryGreen Chemistry |
| spellingShingle | Zhuang Ma Helin Lu Ke Liao Zhilong Chen Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition iScience Pharmaceutical Engineering Organic Chemistry Green Chemistry |
| title | Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition |
| title_full | Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition |
| title_fullStr | Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition |
| title_full_unstemmed | Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition |
| title_short | Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition |
| title_sort | tungstate catalyzed biomimetic oxidative halogenation of hetero arene under mild condition |
| topic | Pharmaceutical Engineering Organic Chemistry Green Chemistry |
| url | http://www.sciencedirect.com/science/article/pii/S2589004220302571 |
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