Electrochemical Dearomatization: Evolution from Chemicals to Traceless Electrons
Dearomatization reactions represent a versatile approach for the preparation of three‐dimensionally (3D) privileged cyclic moieties from simple planar aromatic compounds. However, exogeneous oxidants are required for most of the radical and oxidative dearomatizations. Therefore, sustainable procedur...
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| Published in | Advanced synthesis & catalysis Vol. 362; no. 3; pp. 462 - 477 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Heidelberg
Wiley Subscription Services, Inc
06.02.2020
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| Online Access | Get full text |
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| Abstract | Dearomatization reactions represent a versatile approach for the preparation of three‐dimensionally (3D) privileged cyclic moieties from simple planar aromatic compounds. However, exogeneous oxidants are required for most of the radical and oxidative dearomatizations. Therefore, sustainable procedures are in high demand, especially those in the absence of external oxidizing reagents. Fortunately, electrolytic dearomatization protocols can fulfill the above requirements due to the manipulation of traceless electrons instead of chemicals during the processes. Nevertheless, sustainable electrochemical dearomative transformations have been far less frequently investigated than the well‐developed chemical dearomatization reactions. Herein, we summarize representative breakthroughs in the electrochemical dearomative transformation of indoles, furans and activated arenes (phenols and anisoles) for the synthesis of complicated skeletons. Hopefully, this interesting “simplicity‐to‐complexity” synthetic logic will inspire more innovations from the electroorganic community. |
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| AbstractList | Dearomatization reactions represent a versatile approach for the preparation of three‐dimensionally (3D) privileged cyclic moieties from simple planar aromatic compounds. However, exogeneous oxidants are required for most of the radical and oxidative dearomatizations. Therefore, sustainable procedures are in high demand, especially those in the absence of external oxidizing reagents. Fortunately, electrolytic dearomatization protocols can fulfill the above requirements due to the manipulation of traceless electrons instead of chemicals during the processes. Nevertheless, sustainable electrochemical dearomative transformations have been far less frequently investigated than the well‐developed chemical dearomatization reactions. Herein, we summarize representative breakthroughs in the electrochemical dearomative transformation of indoles, furans and activated arenes (phenols and anisoles) for the synthesis of complicated skeletons. Hopefully, this interesting “simplicity‐to‐complexity” synthetic logic will inspire more innovations from the electroorganic community. Dearomatization reactions represent a versatile approach for the preparation of three‐dimensionally (3D) privileged cyclic moieties from simple planar aromatic compounds. However, exogeneous oxidants are required for most of the radical and oxidative dearomatizations. Therefore, sustainable procedures are in high demand, especially those in the absence of external oxidizing reagents. Fortunately, electrolytic dearomatization protocols can fulfill the above requirements due to the manipulation of traceless electrons instead of chemicals during the processes. Nevertheless, sustainable electrochemical dearomative transformations have been far less frequently investigated than the well‐developed chemical dearomatization reactions. Herein, we summarize representative breakthroughs in the electrochemical dearomative transformation of indoles, furans and activated arenes (phenols and anisoles) for the synthesis of complicated skeletons. Hopefully, this interesting “simplicity‐to‐complexity” synthetic logic will inspire more innovations from the electroorganic community. magnified image |
| Author | Zhang, Guofeng Lv, Shide Chen, Jianbin Gao, Wei |
| Author_xml | – sequence: 1 givenname: Shide surname: Lv fullname: Lv, Shide organization: Qilu University of Technology (Shandong Academy of Sciences) – sequence: 2 givenname: Guofeng surname: Zhang fullname: Zhang, Guofeng organization: Qilu University of Technology (Shandong Academy of Sciences) – sequence: 3 givenname: Jianbin surname: Chen fullname: Chen, Jianbin email: jchen@qlu.edu.cn organization: Qilu University of Technology (Shandong Academy of Sciences) – sequence: 4 givenname: Wei surname: Gao fullname: Gao, Wei organization: Qilu University of Technology (Shandong Academy of Sciences) |
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| Snippet | Dearomatization reactions represent a versatile approach for the preparation of three‐dimensionally (3D) privileged cyclic moieties from simple planar aromatic... |
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| SubjectTerms | Aromatic compounds Chemical reactions dearomatization electrochemistry Electrons Furans Indoles Organic chemistry Oxidation Oxidizing agents Phenols radicals Reagents three-dimensional structures |
| Title | Electrochemical Dearomatization: Evolution from Chemicals to Traceless Electrons |
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