A general electrochemical strategy for the Sandmeyer reaction
Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl , CH I , CCl , LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found t...
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| Veröffentlicht in: | Chemical science (Cambridge) 2018-12, Vol.9 (46), p.8731-8737 |
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| container_title | Chemical science (Cambridge) |
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| creator | Liu, Qianyi Sun, Beiqi Liu, Zheng Kao, Yi Dong, Bo-Wei Jiang, Shang-Da Li, Feng Liu, Guoquan Yang, Yang Mo, Fanyang |
| description | Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl
, CH
I
, CCl
, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and
electron paramagnetic resonance (EPR) analysis. |
| doi_str_mv | 10.1039/c8sc03346c |
| format | Article |
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, CH
I
, CCl
, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and
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, CH
I
, CCl
, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and
electron paramagnetic resonance (EPR) analysis.</description><subject>Aromatic compounds</subject><subject>Carbon tetrachloride</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Electron paramagnetic resonance</subject><subject>Halides</subject><subject>Halogenation</subject><subject>Lithium chloride</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LxDAQhoMoKurFHyAFLyKsTjJt0hwUpPgFggf1HNLsdLfSNpp0hf33xq9FncvMMA8v7_Ayts_hhAPqU1dGB4i5dGtsW0DOJ7JAvb6aBWyxvRifIRUiL4TaZFsIUijUuM3OLrIZDRRsl1FHbgzezalvXdrjGOxIs2XW-JCNc8oe7DDtaUkhC2Td2Pphl200tou099132NPV5WN1M7m7v76tLu4mLgc5TqzgjZUgaglK1LkFoILnesqFkLKoMVeASpGYCoCG21xp6ZqCoIGyFFgL3GHnX7ovi7qnqaMheevMS2h7G5bG29b8vQzt3Mz8m5Gi1Bw-BI6-BYJ_XVAcTd9GR11nB_KLaARXGlEXWiX08B_67BdhSO8lCkslkvU8UcdflAs-xkDNygwH8xGMqcqH6jOYKsEHv-2v0J8Y8B1B3Ybm</recordid><startdate>20181214</startdate><enddate>20181214</enddate><creator>Liu, Qianyi</creator><creator>Sun, Beiqi</creator><creator>Liu, Zheng</creator><creator>Kao, Yi</creator><creator>Dong, Bo-Wei</creator><creator>Jiang, Shang-Da</creator><creator>Li, Feng</creator><creator>Liu, Guoquan</creator><creator>Yang, Yang</creator><creator>Mo, Fanyang</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-0680-4811</orcidid><orcidid>https://orcid.org/0000-0002-4956-2034</orcidid><orcidid>https://orcid.org/0000-0002-4140-3020</orcidid><orcidid>https://orcid.org/0000-0003-0204-9601</orcidid></search><sort><creationdate>20181214</creationdate><title>A general electrochemical strategy for the Sandmeyer reaction</title><author>Liu, Qianyi ; Sun, Beiqi ; Liu, Zheng ; Kao, Yi ; Dong, Bo-Wei ; Jiang, Shang-Da ; Li, Feng ; Liu, Guoquan ; Yang, Yang ; Mo, Fanyang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-a21fa602b6072b4a00e5149d122665b3470377e2d200f1a4796cf5e0f08823b23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aromatic compounds</topic><topic>Carbon tetrachloride</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Electron paramagnetic resonance</topic><topic>Halides</topic><topic>Halogenation</topic><topic>Lithium chloride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Qianyi</creatorcontrib><creatorcontrib>Sun, Beiqi</creatorcontrib><creatorcontrib>Liu, Zheng</creatorcontrib><creatorcontrib>Kao, Yi</creatorcontrib><creatorcontrib>Dong, Bo-Wei</creatorcontrib><creatorcontrib>Jiang, Shang-Da</creatorcontrib><creatorcontrib>Li, Feng</creatorcontrib><creatorcontrib>Liu, Guoquan</creatorcontrib><creatorcontrib>Yang, Yang</creatorcontrib><creatorcontrib>Mo, Fanyang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Qianyi</au><au>Sun, Beiqi</au><au>Liu, Zheng</au><au>Kao, Yi</au><au>Dong, Bo-Wei</au><au>Jiang, Shang-Da</au><au>Li, Feng</au><au>Liu, Guoquan</au><au>Yang, Yang</au><au>Mo, Fanyang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A general electrochemical strategy for the Sandmeyer reaction</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2018-12-14</date><risdate>2018</risdate><volume>9</volume><issue>46</issue><spage>8731</spage><epage>8737</epage><pages>8731-8737</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl
, CH
I
, CCl
, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and
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| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Aromatic compounds Carbon tetrachloride Chemical reactions Chemistry Electron paramagnetic resonance Halides Halogenation Lithium chloride |
| title | A general electrochemical strategy for the Sandmeyer reaction |
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