Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization
Summary: Benzimidazolone constitutes the core structure of numerous pharmaceuticals, agrochemicals, inhibitors, pigments, herbicides, and fine chemicals. Amination of hydrocarbons is an attractive tool for the creation of nitrogen-containing products. However, the multiple steps, harsh conditions, a...
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| Format: | Article |
| Language: | English |
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Elsevier
2019-05-01
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| Series: | iScience |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004219301166 |
| _version_ | 1811318852047339520 |
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| author | Taoyuan Liang He Zhao Lingzhen Gong Huanfeng Jiang Min Zhang |
| author_facet | Taoyuan Liang He Zhao Lingzhen Gong Huanfeng Jiang Min Zhang |
| author_sort | Taoyuan Liang |
| collection | DOAJ |
| description | Summary: Benzimidazolone constitutes the core structure of numerous pharmaceuticals, agrochemicals, inhibitors, pigments, herbicides, and fine chemicals. Amination of hydrocarbons is an attractive tool for the creation of nitrogen-containing products. However, the multiple steps, harsh conditions, and low atom efficiencies often present in these reactions remain challenging. We present a multicomponent synthesis of functional benzimidazolones from arylamines, dialkylamines, and alcohols, acting via the sequence of copper-catalyzed oxidative tandem C–H aminations and alkyl deconstructive carbofunctionalization. The catalytic transformation forms multiple bonds in one single operation, uses readily available feedstocks and a naturally abundant Cu/O2 catalyst system, has broad substrate scope, avoids pre-installation of aminating agents and directing groups, and provides high chemo- and regioselectivity, resulting in direct functionalization of inert C–H and C–C bonds via single-electron oxidation-induced activation mode. This platform can be expected to provide structurally diverse products with interesting biological, chemical, and physical properties. : Chemistry; Catalysis; Organic Chemistry Subject Areas: Chemistry, Catalysis, Organic Chemistry |
| first_indexed | 2024-04-13T12:32:25Z |
| format | Article |
| id | doaj.art-28ceaa36dc8541e3b320af2384f1a373 |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-04-13T12:32:25Z |
| publishDate | 2019-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-28ceaa36dc8541e3b320af2384f1a3732022-12-22T02:46:46ZengElsevieriScience2589-00422019-05-0115127135Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive CarbofunctionalizationTaoyuan Liang0He Zhao1Lingzhen Gong2Huanfeng Jiang3Min Zhang4Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, ChinaKey Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, ChinaKey Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, ChinaKey Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, ChinaKey Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, China; Corresponding authorSummary: Benzimidazolone constitutes the core structure of numerous pharmaceuticals, agrochemicals, inhibitors, pigments, herbicides, and fine chemicals. Amination of hydrocarbons is an attractive tool for the creation of nitrogen-containing products. However, the multiple steps, harsh conditions, and low atom efficiencies often present in these reactions remain challenging. We present a multicomponent synthesis of functional benzimidazolones from arylamines, dialkylamines, and alcohols, acting via the sequence of copper-catalyzed oxidative tandem C–H aminations and alkyl deconstructive carbofunctionalization. The catalytic transformation forms multiple bonds in one single operation, uses readily available feedstocks and a naturally abundant Cu/O2 catalyst system, has broad substrate scope, avoids pre-installation of aminating agents and directing groups, and provides high chemo- and regioselectivity, resulting in direct functionalization of inert C–H and C–C bonds via single-electron oxidation-induced activation mode. This platform can be expected to provide structurally diverse products with interesting biological, chemical, and physical properties. : Chemistry; Catalysis; Organic Chemistry Subject Areas: Chemistry, Catalysis, Organic Chemistryhttp://www.sciencedirect.com/science/article/pii/S2589004219301166 |
| spellingShingle | Taoyuan Liang He Zhao Lingzhen Gong Huanfeng Jiang Min Zhang Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization iScience |
| title | Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization |
| title_full | Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization |
| title_fullStr | Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization |
| title_full_unstemmed | Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization |
| title_short | Synthesis of Multisubstituted Benzimidazolones via Copper-Catalyzed Oxidative Tandem C–H Aminations and Alkyl Deconstructive Carbofunctionalization |
| title_sort | synthesis of multisubstituted benzimidazolones via copper catalyzed oxidative tandem c h aminations and alkyl deconstructive carbofunctionalization |
| url | http://www.sciencedirect.com/science/article/pii/S2589004219301166 |
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