Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C−X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C−O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C...
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| Veröffentlicht in: | Chemistry : a European journal 2020-01, Vol.26 (1), p.176-180 |
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| creator | Klein, Philippe Lechner, Vivien Denise Schimmel, Tanja Hintermann, Lukas |
| description | The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C−X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C−O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C−X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4‐diazadiene catalyst system, in which 1,4‐diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross‐coupling or electrophilic substitution reactions.
Ni–DAD catalyst systems: Unlike aryl halides, common aryl sulfonates do not undergo metal insertion to give organometallic reagents. A nickel‐diazadiene complex has been found to catalyze zincation of aryl sulfonates and provide synthetically valuable arylzinc sulfonates. |
| doi_str_mv | 10.1002/chem.201904545 |
| format | Article |
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Ni–DAD catalyst systems: Unlike aryl halides, common aryl sulfonates do not undergo metal insertion to give organometallic reagents. A nickel‐diazadiene complex has been found to catalyze zincation of aryl sulfonates and provide synthetically valuable arylzinc sulfonates.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201904545</identifier><identifier>PMID: 31591766</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aromatic compounds ; aryl sulfonates ; Bromides ; catalysis ; Catalysts ; Chemistry ; Communication ; Communications ; Cross coupling ; Diacetyl ; Insertion ; Iodides ; metalation ; Nickel ; Nickel chloride ; organozinc reagents ; Reagents ; Room temperature ; Substitution reactions ; Sulfonates ; Zinc ; Zinc dust</subject><ispartof>Chemistry : a European journal, 2020-01, Vol.26 (1), p.176-180</ispartof><rights>2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2019. This article is published under http://creativecommons.org/licenses/by/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><citedby>FETCH-LOGICAL-c5055-59ea2dc4851fdb08679af3363e775ba62e66b05f83582558791686a1f97cb0a33</citedby><cites>FETCH-LOGICAL-c5055-59ea2dc4851fdb08679af3363e775ba62e66b05f83582558791686a1f97cb0a33</cites><orcidid>0000-0002-8485-1472 ; 0000-0003-2622-8663</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.201904545$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201904545$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31591766$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Klein, Philippe</creatorcontrib><creatorcontrib>Lechner, Vivien Denise</creatorcontrib><creatorcontrib>Schimmel, Tanja</creatorcontrib><creatorcontrib>Hintermann, Lukas</creatorcontrib><title>Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C−X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C−O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C−X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4‐diazadiene catalyst system, in which 1,4‐diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross‐coupling or electrophilic substitution reactions.
Ni–DAD catalyst systems: Unlike aryl halides, common aryl sulfonates do not undergo metal insertion to give organometallic reagents. A nickel‐diazadiene complex has been found to catalyze zincation of aryl sulfonates and provide synthetically valuable arylzinc sulfonates.</description><subject>Aromatic compounds</subject><subject>aryl sulfonates</subject><subject>Bromides</subject><subject>catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Communication</subject><subject>Communications</subject><subject>Cross coupling</subject><subject>Diacetyl</subject><subject>Insertion</subject><subject>Iodides</subject><subject>metalation</subject><subject>Nickel</subject><subject>Nickel chloride</subject><subject>organozinc reagents</subject><subject>Reagents</subject><subject>Room temperature</subject><subject>Substitution reactions</subject><subject>Sulfonates</subject><subject>Zinc</subject><subject>Zinc dust</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkUtv1DAUhSMEokNhyxJZYsMmgx-xHW-QqlDaSoVKPDZsLCe5mbp47KmdAJlfj4cpw2PDyov7nU8-OkXxlOAlwZi-7K5hvaSYKFzxit8rFoRTUjIp-P1igVUlS8GZOioepXSDMVaCsYfFESNcESnEonBn4CGa0QaPwoCu4sr4sLW-Q-_BrMCPCbUzeme7L-DQa2u2prc5gZqw3jj4jhozGjdvoUefd6ELnyD-lFk_BnQSZ4c-TG4I3oyQHhcPBuMSPLl7j4tPb04_Nufl5dXZRXNyWXYcc15yBYb2XVVzMvQtroVUZmBMMJCSt0ZQEKLFfKgZrynntVRE1MKQQcmuxYax4-LV3ruZ2jX0Xa4RjdObaNcmzjoYq_--eHutV-GrFkoyKqoseHEniOF2gjTqtU0dOGc8hClpyjCtpKg5z-jzf9CbMEWf62WKEUnzICpTyz3VxZBShOHwGYL1bki9G1IfhsyBZ39WOOC_lsuA2gPfrIP5PzrdnJ--_S3_AWhSqzY</recordid><startdate>20200102</startdate><enddate>20200102</enddate><creator>Klein, Philippe</creator><creator>Lechner, Vivien Denise</creator><creator>Schimmel, Tanja</creator><creator>Hintermann, Lukas</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</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><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-8485-1472</orcidid><orcidid>https://orcid.org/0000-0003-2622-8663</orcidid></search><sort><creationdate>20200102</creationdate><title>Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates</title><author>Klein, Philippe ; Lechner, Vivien Denise ; Schimmel, Tanja ; Hintermann, Lukas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5055-59ea2dc4851fdb08679af3363e775ba62e66b05f83582558791686a1f97cb0a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>aryl sulfonates</topic><topic>Bromides</topic><topic>catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Communication</topic><topic>Communications</topic><topic>Cross coupling</topic><topic>Diacetyl</topic><topic>Insertion</topic><topic>Iodides</topic><topic>metalation</topic><topic>Nickel</topic><topic>Nickel chloride</topic><topic>organozinc reagents</topic><topic>Reagents</topic><topic>Room temperature</topic><topic>Substitution reactions</topic><topic>Sulfonates</topic><topic>Zinc</topic><topic>Zinc dust</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Klein, Philippe</creatorcontrib><creatorcontrib>Lechner, Vivien Denise</creatorcontrib><creatorcontrib>Schimmel, Tanja</creatorcontrib><creatorcontrib>Hintermann, Lukas</creatorcontrib><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library (Open Access Collection)</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Klein, Philippe</au><au>Lechner, Vivien Denise</au><au>Schimmel, Tanja</au><au>Hintermann, Lukas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2020-01-02</date><risdate>2020</risdate><volume>26</volume><issue>1</issue><spage>176</spage><epage>180</epage><pages>176-180</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C−X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C−O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C−X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4‐diazadiene catalyst system, in which 1,4‐diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross‐coupling or electrophilic substitution reactions.
Ni–DAD catalyst systems: Unlike aryl halides, common aryl sulfonates do not undergo metal insertion to give organometallic reagents. A nickel‐diazadiene complex has been found to catalyze zincation of aryl sulfonates and provide synthetically valuable arylzinc sulfonates.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31591766</pmid><doi>10.1002/chem.201904545</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-8485-1472</orcidid><orcidid>https://orcid.org/0000-0003-2622-8663</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Aromatic compounds aryl sulfonates Bromides catalysis Catalysts Chemistry Communication Communications Cross coupling Diacetyl Insertion Iodides metalation Nickel Nickel chloride organozinc reagents Reagents Room temperature Substitution reactions Sulfonates Zinc Zinc dust |
| title | Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates |
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