Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane
A new class of axial-chiral biisoquinoline <i>N</i>,<i>N′</i>-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study re...
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| Format: | Article |
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MDPI AG
2021-09-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/11/9/1103 |
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| author | Shiyu Sun Changgong Xu Jamielyn Jarvis Phillip Nader Brandon Naumann Abigail Soliven Roberto Peverati Norito Takenaka |
| author_facet | Shiyu Sun Changgong Xu Jamielyn Jarvis Phillip Nader Brandon Naumann Abigail Soliven Roberto Peverati Norito Takenaka |
| author_sort | Shiyu Sun |
| collection | DOAJ |
| description | A new class of axial-chiral biisoquinoline <i>N</i>,<i>N′</i>-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (<b>2a</b>–HSiCl<sub>3</sub>) were analyzed using density functional theory calculations. |
| first_indexed | 2024-03-10T07:49:54Z |
| format | Article |
| id | doaj.art-fd283c91506a4645be50e97dca9025b4 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T07:49:54Z |
| publishDate | 2021-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-fd283c91506a4645be50e97dca9025b42023-11-22T12:21:27ZengMDPI AGCatalysts2073-43442021-09-01119110310.3390/catal11091103Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with TrichlorosilaneShiyu Sun0Changgong Xu1Jamielyn Jarvis2Phillip Nader3Brandon Naumann4Abigail Soliven5Roberto Peverati6Norito Takenaka7Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USADepartment of Chemistry, Purdue University, West Lafayette, IN 47907, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USAChemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USAA new class of axial-chiral biisoquinoline <i>N</i>,<i>N′</i>-dioxides was evaluated as catalysts for the enantioselective hydrosilylation of acyl hydrazones with trichlorosilane. While these catalysts provided poor to moderate reactivity and enantioselectivity, this study represents the first example of the organocatalytic asymmetric reduction of acyl hydrazones. In addition, the structures and energies of two possible diastereomeric catalyst–trichlorosilane complexes (<b>2a</b>–HSiCl<sub>3</sub>) were analyzed using density functional theory calculations.https://www.mdpi.com/2073-4344/11/9/1103Lewis base catalysistrichlorosilanehydrosilylationhydrazonecomputational chemistry |
| spellingShingle | Shiyu Sun Changgong Xu Jamielyn Jarvis Phillip Nader Brandon Naumann Abigail Soliven Roberto Peverati Norito Takenaka Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane Catalysts Lewis base catalysis trichlorosilane hydrosilylation hydrazone computational chemistry |
| title | Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane |
| title_full | Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane |
| title_fullStr | Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane |
| title_full_unstemmed | Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane |
| title_short | Evaluation of 3,3′-Triazolyl Biisoquinoline <i>N</i>,<i>N′</i>-Dioxide Catalysts for Asymmetric Hydrosilylation of Hydrazones with Trichlorosilane |
| title_sort | evaluation of 3 3 triazolyl biisoquinoline i n i i n i dioxide catalysts for asymmetric hydrosilylation of hydrazones with trichlorosilane |
| topic | Lewis base catalysis trichlorosilane hydrosilylation hydrazone computational chemistry |
| url | https://www.mdpi.com/2073-4344/11/9/1103 |
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