Scalable Photoelectrochemical Dehydrogenative Cross‐Coupling of Heteroarenes with Aliphatic C−H Bonds
Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross‐coupling of heteroarenes with aliphatic C−H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiom...
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| Published in | Angewandte Chemie International Edition Vol. 59; no. 34; pp. 14275 - 14280 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
17.08.2020
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross‐coupling of heteroarenes with aliphatic C−H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross‐coupling of heteroarenes and C(sp3)−H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3)−H donor is converted to a nucleophilic carbon radical through H‐atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl−. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products.
An efficient photoelectrochemical dehydrogenative cross‐coupling of heteroarenes with C(sp3)−H species is described. Chlorine atoms, which are produced by light irradiation of anodically generated Cl2 from Cl−, a hydrogen atom from C(sp3)−H bonds to afford carbon radicals. The latter undergo Minisci alkylation to afford the final functionalized heteroarene products. |
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| AbstractList | Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross‐coupling of heteroarenes with aliphatic C−H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross‐coupling of heteroarenes and C(sp3)−H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3)−H donor is converted to a nucleophilic carbon radical through H‐atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl−. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products. Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C-H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross-coupling of heteroarenes and C(sp(3))-H donors through H(2)evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp(3))-H donor is converted to a nucleophilic carbon radical through H-atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl(2)from Cl-. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products. Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross‐coupling of heteroarenes with aliphatic C−H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross‐coupling of heteroarenes and C(sp3)−H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3)−H donor is converted to a nucleophilic carbon radical through H‐atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl−. The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products. An efficient photoelectrochemical dehydrogenative cross‐coupling of heteroarenes with C(sp3)−H species is described. Chlorine atoms, which are produced by light irradiation of anodically generated Cl2 from Cl−, a hydrogen atom from C(sp3)−H bonds to afford carbon radicals. The latter undergo Minisci alkylation to afford the final functionalized heteroarene products. Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross‐coupling of heteroarenes with aliphatic C−H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross‐coupling of heteroarenes and C(sp 3 )−H donors through H 2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp 3 )−H donor is converted to a nucleophilic carbon radical through H‐atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl 2 from Cl − . The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products. Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C-H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross-coupling of heteroarenes and C(sp3 )-H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3 )-H donor is converted to a nucleophilic carbon radical through H-atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl- . The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products.Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic C-H bonds provides straightforward access to functionalized heteroarenes from readily available materials. Established methods employ stoichiometric chemical oxidants under conditions of heating or light irradiation. By merging electrochemistry and photochemistry, we have achieved efficient photoelectrochemical dehydrogenative cross-coupling of heteroarenes and C(sp3 )-H donors through H2 evolution, without the addition of metal catalysts or chemical oxidants. Mechanistically, the C(sp3 )-H donor is converted to a nucleophilic carbon radical through H-atom transfer with chlorine atom, which is produced by light irradiation of anodically generated Cl2 from Cl- . The carbon radical then undergoes radical substitution to the heteroarene to afford alkylated heteroarene products. |
| Author | Chen, Peng‐Yu Xu, Pin Xu, Hai‐Chao |
| Author_xml | – sequence: 1 givenname: Pin surname: Xu fullname: Xu, Pin organization: Xiamen University – sequence: 2 givenname: Peng‐Yu surname: Chen fullname: Chen, Peng‐Yu organization: Xiamen University – sequence: 3 givenname: Hai‐Chao orcidid: 0000-0002-3008-5143 surname: Xu fullname: Xu, Hai‐Chao email: haichao.xu@xmu.edu.cn organization: Xiamen University |
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| ContentType | Journal Article |
| Copyright | 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2020 Wiley‐VCH GmbH 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| DOI | 10.1002/anie.202005724 |
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| Edition | International ed. in English |
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| ISSN | 1433-7851 1521-3773 |
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| Issue | 34 |
| Keywords | ELECTROSYNTHESIS CATALYSIS photoelectrochemistry electrochemistry LIGHT ARYLATION radical reactions C-H functionalization FUNCTIONALIZATION heterocycles GENERATION ARYL CHLORIDES ALKANES |
| Language | English |
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| SSID | ssj0028806 |
| Score | 2.6715763 |
| Snippet | Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross‐coupling of heteroarenes with aliphatic... Heteroarenes are structural motifs found in many bioactive compounds and functional materials. Dehydrogenative cross-coupling of heteroarenes with aliphatic... |
| Source | Web of Science |
| SourceID | proquest webofscience crossref wiley |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 14275 |
| SubjectTerms | Aliphatic compounds Alkylation Bioactive compounds Carbon Catalysts Chemical bonds Chemistry Chemistry, Multidisciplinary Chlorine Coupling (molecular) Cross coupling C−H functionalization Dehydrogenation Electrochemistry Functional materials heterocycles Hydrogen evolution Irradiation Light irradiation Oxidants Oxidizing agents Photochemistry photoelectrochemistry Physical Sciences Radiation radical reactions Radicals Science & Technology |
| Title | Scalable Photoelectrochemical Dehydrogenative Cross‐Coupling of Heteroarenes with Aliphatic C−H Bonds |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202005724 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000546461800001 https://www.proquest.com/docview/2431727990 https://www.proquest.com/docview/2409189434 |
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