Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis
Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amid...
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| Published in | Nature communications Vol. 11; no. 1; pp. 1249 - 9 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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London
Nature Publishing Group UK
06.03.2020
Nature Publishing Group Nature Portfolio |
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| Abstract | Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H
3
N·BH
3
at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H
3
N·BH
3
to the N=C bond of the substrates.
Controlling the partial reduction of quinolines is challenging, given the competing overreduction to tetrahydroquinolines. Here, the authors report a cobalt-amido cooperative catalyst for the selective, partial transfer hydrogenation of quinolines to 1,2-dihydroquinolines with H
3
N·BH
3
as reductant. |
|---|---|
| AbstractList | Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H3N·BH3 at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H3N·BH3 to the N=C bond of the substrates.Controlling the partial reduction of quinolines is challenging, given the competing overreduction to tetrahydroquinolines. Here, the authors report a cobalt-amido cooperative catalyst for the selective, partial transfer hydrogenation of quinolines to 1,2-dihydroquinolines with H3N·BH3 as reductant. Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H N·BH at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H N·BH to the N=C bond of the substrates. Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H 3 N·BH 3 at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H 3 N·BH 3 to the N=C bond of the substrates. Controlling the partial reduction of quinolines is challenging, given the competing overreduction to tetrahydroquinolines. Here, the authors report a cobalt-amido cooperative catalyst for the selective, partial transfer hydrogenation of quinolines to 1,2-dihydroquinolines with H 3 N·BH 3 as reductant. Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H3N·BH3 at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H3N·BH3 to the N=C bond of the substrates.Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H3N·BH3 at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H3N·BH3 to the N=C bond of the substrates. Controlling the partial reduction of quinolines is challenging, given the competing overreduction to tetrahydroquinolines. Here, the authors report a cobalt-amido cooperative catalyst for the selective, partial transfer hydrogenation of quinolines to 1,2-dihydroquinolines with H3N·BH3 as reductant. Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H 3 N·BH 3 at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H 3 N·BH 3 to the N=C bond of the substrates. |
| ArticleNumber | 1249 |
| Author | Pang, Maofu Liao, Rong-Zhen Chen, Jia-Yi Tung, Chen-Ho Wang, Wenguang Zhang, Shengjie |
| Author_xml | – sequence: 1 givenname: Maofu surname: Pang fullname: Pang, Maofu organization: Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University – sequence: 2 givenname: Jia-Yi surname: Chen fullname: Chen, Jia-Yi organization: School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology – sequence: 3 givenname: Shengjie surname: Zhang fullname: Zhang, Shengjie organization: Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University – sequence: 4 givenname: Rong-Zhen surname: Liao fullname: Liao, Rong-Zhen email: rongzhen@hust.edu.cn organization: School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology – sequence: 5 givenname: Chen-Ho surname: Tung fullname: Tung, Chen-Ho organization: Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University – sequence: 6 givenname: Wenguang orcidid: 0000-0002-4108-7865 surname: Wang fullname: Wang, Wenguang email: wwg@sdu.edu.cn organization: Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32144242$$D View this record in MEDLINE/PubMed |
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| Snippet | Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to... Controlling the partial reduction of quinolines is challenging, given the competing overreduction to tetrahydroquinolines. Here, the authors report a... |
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| SubjectTerms | 119/118 140/131 140/58 639/638/549/933 639/638/77/885 639/638/77/888 Catalysis Catalysts Cobalt Functional groups Humanities and Social Sciences Hydrogenation multidisciplinary Organic compounds Quinoline Quinolines Reduction Regioselectivity Room temperature Science Science (multidisciplinary) Substrates |
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| Title | Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis |
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