Enantioselective Hydroxylation of Dihydrosilanes to Si‐Chiral Silanols Catalyzed by In Situ Generated Copper(II) Species
Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si‐chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single‐electron transfer...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 32; pp. e202205743 - n/a |
|---|---|
| Main Authors | , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
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08.08.2022
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| Edition | International ed. in English |
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| Abstract | Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si‐chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single‐electron transfer (SET) oxidant for invoking CuII species and chiral multidentate anionic N,N,P‐ligands for effective enantiocontrol. The reaction readily provides a broad range of Si‐chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si‐chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral CuII species as the active catalyst and its subsequent σ‐metathesis with dihydrosilanes.
Copper(II)‐mediated σ‐metathesis with prochiral dihydrosilanes has been successfully leveraged to efficiently synthesize Si‐chiral silanols as well as many other related Si‐chiral skeletons. The reaction hinges on the continuous generation of catalytically active copper(II) species via single‐electron transfer oxidation of copper(I) by alkyl halides and the efficient stereocontrol with multidentate anionic N,N,P‐ligands. |
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| AbstractList | Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si‐chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single‐electron transfer (SET) oxidant for invoking Cu
II
species and chiral multidentate anionic N,N,P‐ligands for effective enantiocontrol. The reaction readily provides a broad range of Si‐chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si‐chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral Cu
II
species as the active catalyst and its subsequent
σ
‐metathesis with dihydrosilanes. Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si‐chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single‐electron transfer (SET) oxidant for invoking CuII species and chiral multidentate anionic N,N,P‐ligands for effective enantiocontrol. The reaction readily provides a broad range of Si‐chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si‐chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral CuII species as the active catalyst and its subsequent σ‐metathesis with dihydrosilanes.Dedicated to Prof. Chi-Ming Che on the occasion of his 65th birthday. Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si‐chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single‐electron transfer (SET) oxidant for invoking CuII species and chiral multidentate anionic N,N,P‐ligands for effective enantiocontrol. The reaction readily provides a broad range of Si‐chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si‐chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral CuII species as the active catalyst and its subsequent σ‐metathesis with dihydrosilanes. Copper(II)‐mediated σ‐metathesis with prochiral dihydrosilanes has been successfully leveraged to efficiently synthesize Si‐chiral silanols as well as many other related Si‐chiral skeletons. The reaction hinges on the continuous generation of catalytically active copper(II) species via single‐electron transfer oxidation of copper(I) by alkyl halides and the efficient stereocontrol with multidentate anionic N,N,P‐ligands. Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si-chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single-electron transfer (SET) oxidant for invoking Cu-II species and chiral multidentate anionic N,N,P-ligands for effective enantiocontrol. The reaction readily provides a broad range of Si-chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si-chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral Cu-II species as the active catalyst and its subsequent sigma-metathesis with dihydrosilanes. Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si-chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single-electron transfer (SET) oxidant for invoking CuII species and chiral multidentate anionic N,N,P-ligands for effective enantiocontrol. The reaction readily provides a broad range of Si-chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si-chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral CuII species as the active catalyst and its subsequent σ-metathesis with dihydrosilanes. Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si-chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single-electron transfer (SET) oxidant for invoking CuII species and chiral multidentate anionic N,N,P-ligands for effective enantiocontrol. The reaction readily provides a broad range of Si-chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si-chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral CuII species as the active catalyst and its subsequent σ-metathesis with dihydrosilanes.Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si-chiral silanols, yet has remained unknown up to date. Herein, we describe a strategy for realizing this reaction: using an alkyl bromide as a single-electron transfer (SET) oxidant for invoking CuII species and chiral multidentate anionic N,N,P-ligands for effective enantiocontrol. The reaction readily provides a broad range of Si-chiral silanols with high enantioselectivity and excellent functional group compatibility. In addition, we manifest the synthetic potential by establishing two synthetic schemes for transforming the obtained products into Si-chiral compounds with high structural diversity. Our preliminary mechanistic studies support a mechanism involving SET for recruiting chiral CuII species as the active catalyst and its subsequent σ-metathesis with dihydrosilanes. |
| ArticleNumber | 202205743 |
| Author | Wang, Shou‐Guo Guo, Jiandong He, Chuan Yang, Wu Tian, Yu Wang, Xiaotai Zhang, Jia‐Yong Liu, Lin Wang, Li‐Lei Li, Zhong‐Liang Liu, Xin‐Yuan Gu, Qiang‐Shuai Luan, Cheng Fan, Li‐Wen |
| Author_xml | – sequence: 1 givenname: Wu surname: Yang fullname: Yang, Wu organization: Chinese Academy of Sciences – sequence: 2 givenname: Lin surname: Liu fullname: Liu, Lin organization: Great Bay University – sequence: 3 givenname: Jiandong surname: Guo fullname: Guo, Jiandong organization: Hoffmann Institute of Advanced Materials – sequence: 4 givenname: Shou‐Guo surname: Wang fullname: Wang, Shou‐Guo organization: Chinese Academy of Sciences – sequence: 5 givenname: Jia‐Yong surname: Zhang fullname: Zhang, Jia‐Yong organization: Southern University of Science and Technology – sequence: 6 givenname: Li‐Wen surname: Fan fullname: Fan, Li‐Wen organization: Southern University of Science and Technology – sequence: 7 givenname: Yu surname: Tian fullname: Tian, Yu organization: Southern University of Science and Technology – sequence: 8 givenname: Li‐Lei surname: Wang fullname: Wang, Li‐Lei organization: Southern University of Science and Technology – sequence: 9 givenname: Cheng surname: Luan fullname: Luan, Cheng organization: Southern University of Science and Technology – sequence: 10 givenname: Zhong‐Liang surname: Li fullname: Li, Zhong‐Liang organization: Southern University of Science and Technology – sequence: 11 givenname: Chuan surname: He fullname: He, Chuan organization: Southern University of Science and Technology – sequence: 12 givenname: Xiaotai orcidid: 0000-0003-3310-3308 surname: Wang fullname: Wang, Xiaotai email: xiaotai.wang@ucdenver.edu organization: University of Colorado Denver – sequence: 13 givenname: Qiang‐Shuai surname: Gu fullname: Gu, Qiang‐Shuai email: guqs@sustech.edu.cn organization: Southern University of Science and Technology – sequence: 14 givenname: Xin‐Yuan orcidid: 0000-0002-6978-6465 surname: Liu fullname: Liu, Xin‐Yuan email: liuxy3@sustech.edu.cn organization: Southern University of Science and Technology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35652388$$D View this record in MEDLINE/PubMed |
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| Keywords | Single-Electron Transfer (SET) Oxidation ASYMMETRIC-SYNTHESIS Metathesis CLASSIFICATION C-H SILYLATION SILICON-STEREOGENIC SILANES COORDINATION-COMPOUNDS ALKENES Asymmetric Catalysis Silanols KINETIC RESOLUTION Copper ACCESS STRUCTURAL DATA 1,2-DIFUNCTIONALIZATION silanols single-electron transfer (SET) oxidation copper asymmetric catalysis metathesis |
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| Snippet | Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si‐chiral silanols, yet has... Catalytic enantioselective hydroxylation of prochiral dihydrosilanes with water is expected to be a highly efficient way to access Si-chiral silanols, yet has... |
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| SubjectTerms | Asymmetric Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Copper Electron transfer Enantiomers Functional groups Hydroxylation Metathesis Oxidants Oxidizing agents Physical Sciences Science & Technology Silanols Silicon compounds Single-Electron Transfer (SET) Oxidation Species |
| Title | Enantioselective Hydroxylation of Dihydrosilanes to Si‐Chiral Silanols Catalyzed by In Situ Generated Copper(II) Species |
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