Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes
An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed. The electrochemical methodology uses only imidazolium salts, gold metal electrodes, and electricity to produce these complexes with hydrogen gas as the only by‐product. This high‐yielding and operat...
Gespeichert in:
Veröffentlicht in: | Chemistry : a European journal 2024-01, Vol.30 (2), p.e202303161-n/a |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | n/a |
---|---|
container_issue | 2 |
container_start_page | e202303161 |
container_title | Chemistry : a European journal |
container_volume | 30 |
creator | Nicholls, Thomas P. Jia, Zhongfan Chalker, Justin M. |
description | An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed. The electrochemical methodology uses only imidazolium salts, gold metal electrodes, and electricity to produce these complexes with hydrogen gas as the only by‐product. This high‐yielding and operationally simple procedure has been used to produce eight mononuclear and three dinuclear Au‐NHC complexes. The electrochemical procedure facilitates a clean reaction with no by‐products. As such, Au‐NHC complexes can be directly transferred to catalytic reactions without work‐up or purification. The Au‐NHC complexes were produced on‐demand and tested as catalysts in a vinylcyclopropanation reaction. All mononuclear Au‐NHC complexes performed similarly to or better than the isolated complexes.
An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed in which the only by‐product is hydrogen gas. This enables the clean Au‐NHC complexes to be transferred directly to subsequent catalytic reactions without extra work‐up. This telescoped methodology has been showcased for several mononuclear and dinuclear Au‐NHC complexes in a catalytic vinylcyclopropanation reaction, delivering high yields and demonstrating procedural simplicity. |
doi_str_mv | 10.1002/chem.202303161 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2881712465</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2911642478</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3681-4c888e763dbb59b795efd03184e25da42395b64f1fbad0dffbcba28c441e72503</originalsourceid><addsrcrecordid>eNqFkLtOw0AQRVcIREKgpUSWaGgc9uV9lMjKAylAAdQr73qsOFrHwZsI3PEJfCNfgqMEkGgoRtOcObpzEToneEgwptduDtWQYsowI4IcoD5JKImZFMkh6mPNZSwSpnvoJIQFxlgLxo5Rj0klBaa6j8YjD27d1FtP6TIfPbbL9RxCGaK6iCa1zz_fP-67mcIaOqx1vnRRmjUWlhCldbXy8AbhFB0VmQ9wtt8D9DwePaXTePYwuU1vZrFjQpGYO6UUSMFyaxNtpU6gyLvkigNN8oxTphMreEEKm-U4LwrrbEaV45yApAlmA3S1866a-mUDYW2qMjjwPltCvQmGKkUkobx7eoAu_6CLetMsu3SGakIEp1yqjhruKNfUITRQmFVTVlnTGoLNtmGzbcb8NNwdXOy1G1tB_oN_V9oBege8lh7af3QmnY7ufuVffdyI3w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2911642478</pqid></control><display><type>article</type><title>Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Nicholls, Thomas P. ; Jia, Zhongfan ; Chalker, Justin M.</creator><creatorcontrib>Nicholls, Thomas P. ; Jia, Zhongfan ; Chalker, Justin M.</creatorcontrib><description>An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed. The electrochemical methodology uses only imidazolium salts, gold metal electrodes, and electricity to produce these complexes with hydrogen gas as the only by‐product. This high‐yielding and operationally simple procedure has been used to produce eight mononuclear and three dinuclear Au‐NHC complexes. The electrochemical procedure facilitates a clean reaction with no by‐products. As such, Au‐NHC complexes can be directly transferred to catalytic reactions without work‐up or purification. The Au‐NHC complexes were produced on‐demand and tested as catalysts in a vinylcyclopropanation reaction. All mononuclear Au‐NHC complexes performed similarly to or better than the isolated complexes.
An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed in which the only by‐product is hydrogen gas. This enables the clean Au‐NHC complexes to be transferred directly to subsequent catalytic reactions without extra work‐up. This telescoped methodology has been showcased for several mononuclear and dinuclear Au‐NHC complexes in a catalytic vinylcyclopropanation reaction, delivering high yields and demonstrating procedural simplicity.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202303161</identifier><identifier>PMID: 37876029</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Carbenes ; catalysis ; Catalysts ; Chemical synthesis ; Chemistry ; Electrochemistry ; Gold ; N-Heterocyclic carbene ; synthesis</subject><ispartof>Chemistry : a European journal, 2024-01, Vol.30 (2), p.e202303161-n/a</ispartof><rights>2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><rights>2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.</rights><rights>2023. This article is published under http://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3681-4c888e763dbb59b795efd03184e25da42395b64f1fbad0dffbcba28c441e72503</cites><orcidid>0000-0001-6654-0825 ; 0000-0001-9690-7288 ; 0000-0002-7504-5508</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202303161$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202303161$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37876029$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nicholls, Thomas P.</creatorcontrib><creatorcontrib>Jia, Zhongfan</creatorcontrib><creatorcontrib>Chalker, Justin M.</creatorcontrib><title>Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed. The electrochemical methodology uses only imidazolium salts, gold metal electrodes, and electricity to produce these complexes with hydrogen gas as the only by‐product. This high‐yielding and operationally simple procedure has been used to produce eight mononuclear and three dinuclear Au‐NHC complexes. The electrochemical procedure facilitates a clean reaction with no by‐products. As such, Au‐NHC complexes can be directly transferred to catalytic reactions without work‐up or purification. The Au‐NHC complexes were produced on‐demand and tested as catalysts in a vinylcyclopropanation reaction. All mononuclear Au‐NHC complexes performed similarly to or better than the isolated complexes.
An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed in which the only by‐product is hydrogen gas. This enables the clean Au‐NHC complexes to be transferred directly to subsequent catalytic reactions without extra work‐up. This telescoped methodology has been showcased for several mononuclear and dinuclear Au‐NHC complexes in a catalytic vinylcyclopropanation reaction, delivering high yields and demonstrating procedural simplicity.</description><subject>Carbenes</subject><subject>catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Electrochemistry</subject><subject>Gold</subject><subject>N-Heterocyclic carbene</subject><subject>synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkLtOw0AQRVcIREKgpUSWaGgc9uV9lMjKAylAAdQr73qsOFrHwZsI3PEJfCNfgqMEkGgoRtOcObpzEToneEgwptduDtWQYsowI4IcoD5JKImZFMkh6mPNZSwSpnvoJIQFxlgLxo5Rj0klBaa6j8YjD27d1FtP6TIfPbbL9RxCGaK6iCa1zz_fP-67mcIaOqx1vnRRmjUWlhCldbXy8AbhFB0VmQ9wtt8D9DwePaXTePYwuU1vZrFjQpGYO6UUSMFyaxNtpU6gyLvkigNN8oxTphMreEEKm-U4LwrrbEaV45yApAlmA3S1866a-mUDYW2qMjjwPltCvQmGKkUkobx7eoAu_6CLetMsu3SGakIEp1yqjhruKNfUITRQmFVTVlnTGoLNtmGzbcb8NNwdXOy1G1tB_oN_V9oBege8lh7af3QmnY7ufuVffdyI3w</recordid><startdate>20240108</startdate><enddate>20240108</enddate><creator>Nicholls, Thomas P.</creator><creator>Jia, Zhongfan</creator><creator>Chalker, Justin M.</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6654-0825</orcidid><orcidid>https://orcid.org/0000-0001-9690-7288</orcidid><orcidid>https://orcid.org/0000-0002-7504-5508</orcidid></search><sort><creationdate>20240108</creationdate><title>Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes</title><author>Nicholls, Thomas P. ; Jia, Zhongfan ; Chalker, Justin M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3681-4c888e763dbb59b795efd03184e25da42395b64f1fbad0dffbcba28c441e72503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Carbenes</topic><topic>catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Electrochemistry</topic><topic>Gold</topic><topic>N-Heterocyclic carbene</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nicholls, Thomas P.</creatorcontrib><creatorcontrib>Jia, Zhongfan</creatorcontrib><creatorcontrib>Chalker, Justin M.</creatorcontrib><collection>Wiley Online Library Open Access</collection><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>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nicholls, Thomas P.</au><au>Jia, Zhongfan</au><au>Chalker, Justin M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2024-01-08</date><risdate>2024</risdate><volume>30</volume><issue>2</issue><spage>e202303161</spage><epage>n/a</epage><pages>e202303161-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed. The electrochemical methodology uses only imidazolium salts, gold metal electrodes, and electricity to produce these complexes with hydrogen gas as the only by‐product. This high‐yielding and operationally simple procedure has been used to produce eight mononuclear and three dinuclear Au‐NHC complexes. The electrochemical procedure facilitates a clean reaction with no by‐products. As such, Au‐NHC complexes can be directly transferred to catalytic reactions without work‐up or purification. The Au‐NHC complexes were produced on‐demand and tested as catalysts in a vinylcyclopropanation reaction. All mononuclear Au‐NHC complexes performed similarly to or better than the isolated complexes.
An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed in which the only by‐product is hydrogen gas. This enables the clean Au‐NHC complexes to be transferred directly to subsequent catalytic reactions without extra work‐up. This telescoped methodology has been showcased for several mononuclear and dinuclear Au‐NHC complexes in a catalytic vinylcyclopropanation reaction, delivering high yields and demonstrating procedural simplicity.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>37876029</pmid><doi>10.1002/chem.202303161</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-6654-0825</orcidid><orcidid>https://orcid.org/0000-0001-9690-7288</orcidid><orcidid>https://orcid.org/0000-0002-7504-5508</orcidid><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0947-6539 |
ispartof | Chemistry : a European journal, 2024-01, Vol.30 (2), p.e202303161-n/a |
issn | 0947-6539 1521-3765 |
language | eng |
recordid | cdi_proquest_miscellaneous_2881712465 |
source | Wiley Online Library Journals Frontfile Complete |
subjects | Carbenes catalysis Catalysts Chemical synthesis Chemistry Electrochemistry Gold N-Heterocyclic carbene synthesis |
title | Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T14%3A09%3A15IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Electrochemical%20Synthesis%20of%20Gold%E2%80%90N%E2%80%90Heterocyclic%20Carbene%20Complexes&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Nicholls,%20Thomas%20P.&rft.date=2024-01-08&rft.volume=30&rft.issue=2&rft.spage=e202303161&rft.epage=n/a&rft.pages=e202303161-n/a&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.202303161&rft_dat=%3Cproquest_cross%3E2911642478%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2911642478&rft_id=info:pmid/37876029&rfr_iscdi=true |