Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes
Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyan...
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| Veröffentlicht in: | Chemistry : a European journal 2021-07, Vol.27 (37), p.9694-9699 |
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| container_title | Chemistry : a European journal |
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| creator | Gärtner, Annalena Marek, Matthäus Arrowsmith, Merle Auerhammer, Dominic Radacki, Krzysztof Prieschl, Dominic Dewhurst, Rian D. Braunschweig, Holger |
| description | Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes.
Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of the corresponding (cyano)dihydroborane precursors. They display boron‐centered nucleophilic reactivity towards organohalides but cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of the first linear 2‐aza‐1,4‐diborabutatrienes. |
| doi_str_mv | 10.1002/chem.202101025 |
| format | Article |
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Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of the corresponding (cyano)dihydroborane precursors. They display boron‐centered nucleophilic reactivity towards organohalides but cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of the first linear 2‐aza‐1,4‐diborabutatrienes.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202101025</identifier><identifier>PMID: 33830542</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Anions ; Boron ; boryl anion ; Chemistry ; cumulene ; Nitrogen ; nucleophile ; Reactivity</subject><ispartof>Chemistry : a European journal, 2021-07, Vol.27 (37), p.9694-9699</ispartof><rights>2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH</rights><rights>2021. 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-c4455-4ecff520d53a0775457823de7459c290554a9068a860728b600d8ce14e79987e3</citedby><cites>FETCH-LOGICAL-c4455-4ecff520d53a0775457823de7459c290554a9068a860728b600d8ce14e79987e3</cites><orcidid>0000-0001-5978-811X ; 0000-0001-9264-1726</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.202101025$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202101025$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Gärtner, Annalena</creatorcontrib><creatorcontrib>Marek, Matthäus</creatorcontrib><creatorcontrib>Arrowsmith, Merle</creatorcontrib><creatorcontrib>Auerhammer, Dominic</creatorcontrib><creatorcontrib>Radacki, Krzysztof</creatorcontrib><creatorcontrib>Prieschl, Dominic</creatorcontrib><creatorcontrib>Dewhurst, Rian D.</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><title>Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes</title><title>Chemistry : a European journal</title><description>Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes.
Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of the corresponding (cyano)dihydroborane precursors. They display boron‐centered nucleophilic reactivity towards organohalides but cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of the first linear 2‐aza‐1,4‐diborabutatrienes.</description><subject>Anions</subject><subject>Boron</subject><subject>boryl anion</subject><subject>Chemistry</subject><subject>cumulene</subject><subject>Nitrogen</subject><subject>nucleophile</subject><subject>Reactivity</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFks1u1DAQxyMEotvClbMlLluJXRx_JhyQlqhQpFIkPs6W15lsXGXtrZ0sSk88Ai_Bi_EkON2qCC5cxrLnN__x2P8se5bjZY4xeWla2C4JJjnOMeEPslnOSb6gUvCH2QyXTC4Ep-VRdhzjFca4FJQ-zo4oLSjmjMyyn2988O7X9x9oDyEOEV3aPvgNTEcVuB4C1OhyMB34XWs7a9An0Ka3e9uPyDdoXo3a-dN2rINf-zB2aOWsd_EV-jy6voVo44TdUvNb6tSHTdokWDuISLsakdRsdaNTzF-wFGs7ZddDr_tgIVFPskeN7iI8vVtPsq9vz75U54uLj-_eV6uLhWGM8wUD0zSc4JpTjaXkjMuC0Bok46UhJeac6RKLQhcCS1KsBcZ1YSBnIMuykEBPstcH3d2w3kJt0gME3aldsFsdRuW1VX9nnG3Vxu9VQQXBhUwC8zuB4K8HiL3a2mig69KsfoiK8OmbeEmKhD7_B73yQ3BpvEQxyYUQdBJcHigTfIwBmvvL5FhNDlCTA9S9A1JBeSj4ZjsY_0Or6vzsw5_a36E7uqY</recordid><startdate>20210702</startdate><enddate>20210702</enddate><creator>Gärtner, Annalena</creator><creator>Marek, Matthäus</creator><creator>Arrowsmith, Merle</creator><creator>Auerhammer, Dominic</creator><creator>Radacki, Krzysztof</creator><creator>Prieschl, Dominic</creator><creator>Dewhurst, Rian D.</creator><creator>Braunschweig, Holger</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</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/0000-0001-5978-811X</orcidid><orcidid>https://orcid.org/0000-0001-9264-1726</orcidid></search><sort><creationdate>20210702</creationdate><title>Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes</title><author>Gärtner, Annalena ; Marek, Matthäus ; Arrowsmith, Merle ; Auerhammer, Dominic ; Radacki, Krzysztof ; Prieschl, Dominic ; Dewhurst, Rian D. ; Braunschweig, Holger</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4455-4ecff520d53a0775457823de7459c290554a9068a860728b600d8ce14e79987e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Anions</topic><topic>Boron</topic><topic>boryl anion</topic><topic>Chemistry</topic><topic>cumulene</topic><topic>Nitrogen</topic><topic>nucleophile</topic><topic>Reactivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gärtner, Annalena</creatorcontrib><creatorcontrib>Marek, Matthäus</creatorcontrib><creatorcontrib>Arrowsmith, Merle</creatorcontrib><creatorcontrib>Auerhammer, Dominic</creatorcontrib><creatorcontrib>Radacki, Krzysztof</creatorcontrib><creatorcontrib>Prieschl, Dominic</creatorcontrib><creatorcontrib>Dewhurst, Rian D.</creatorcontrib><creatorcontrib>Braunschweig, Holger</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</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>Gärtner, Annalena</au><au>Marek, Matthäus</au><au>Arrowsmith, Merle</au><au>Auerhammer, Dominic</au><au>Radacki, Krzysztof</au><au>Prieschl, Dominic</au><au>Dewhurst, Rian D.</au><au>Braunschweig, Holger</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes</atitle><jtitle>Chemistry : a European journal</jtitle><date>2021-07-02</date><risdate>2021</risdate><volume>27</volume><issue>37</issue><spage>9694</spage><epage>9699</epage><pages>9694-9699</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of (cyano)dihydroborane precursors. While they display boron‐centered nucleophilic reactivity towards organohalides, generating fully unsymmetrically substituted cyano(hydro)organoboranes, they show cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of hitherto unknown linear 2‐aza‐1,4‐diborabutatrienes.
Cyclic alkyl(amino)carbene‐stabilized (cyano)hydroboryl anions were synthesized by deprotonation of the corresponding (cyano)dihydroborane precursors. They display boron‐centered nucleophilic reactivity towards organohalides but cyano‐nitrogen‐centered nucleophilic reactivity towards haloboranes, resulting in the formation of the first linear 2‐aza‐1,4‐diborabutatrienes.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><pmid>33830542</pmid><doi>10.1002/chem.202101025</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-5978-811X</orcidid><orcidid>https://orcid.org/0000-0001-9264-1726</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Anions Boron boryl anion Chemistry cumulene Nitrogen nucleophile Reactivity |
| title | Boron‐ versus Nitrogen‐Centered Nucleophilic Reactivity of (Cyano)hydroboryl Anions: Synthesis of Cyano(hydro)organoboranes and 2‐Aza‐1,4‐diborabutatrienes |
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