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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry : a European journal 2024-01, Vol.30 (2), p.e202303161-n/a
Hauptverfasser: Nicholls, Thomas P., Jia, Zhongfan, Chalker, Justin M.
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 &amp; 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