N‐Heterocyclic Carbene Acyl Anion Organocatalysis by Ball‐Milling
The ability to conduct N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter react...
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| Veröffentlicht in: | ChemSusChem 2020-01, Vol.13 (1), p.131-135 |
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| creator | Nicholson, William I. Seastram, Alex C. Iqbal, Saqib A. Reed‐Berendt, Benjamin G. Morrill, Louis C. Browne, Duncan L. |
| description | The ability to conduct N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent‐minimised conditions.
Having a ball: The ability to conduct mechanistically complex N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process is exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples. |
| doi_str_mv | 10.1002/cssc.201902346 |
| format | Article |
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Having a ball: The ability to conduct mechanistically complex N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process is exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.201902346</identifier><identifier>PMID: 31774627</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>acyl anion ; Anions ; ball milling ; Benzoin ; Communication ; Communications ; mechanochemistry ; N-heterocyclic carbenes ; Organic chemistry ; organocatalysis</subject><ispartof>ChemSusChem, 2020-01, Vol.13 (1), p.131-135</ispartof><rights>2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5056-65ddfa61f1afde69ffc72c6b9aacb0d4a9a62a9255ac75711cfb79a6bf109a133</citedby><cites>FETCH-LOGICAL-c5056-65ddfa61f1afde69ffc72c6b9aacb0d4a9a62a9255ac75711cfb79a6bf109a133</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcssc.201902346$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.201902346$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31774627$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nicholson, William I.</creatorcontrib><creatorcontrib>Seastram, Alex C.</creatorcontrib><creatorcontrib>Iqbal, Saqib A.</creatorcontrib><creatorcontrib>Reed‐Berendt, Benjamin G.</creatorcontrib><creatorcontrib>Morrill, Louis C.</creatorcontrib><creatorcontrib>Browne, Duncan L.</creatorcontrib><title>N‐Heterocyclic Carbene Acyl Anion Organocatalysis by Ball‐Milling</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>The ability to conduct N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent‐minimised conditions.
Having a ball: The ability to conduct mechanistically complex N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process is exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples.</description><subject>acyl anion</subject><subject>Anions</subject><subject>ball milling</subject><subject>Benzoin</subject><subject>Communication</subject><subject>Communications</subject><subject>mechanochemistry</subject><subject>N-heterocyclic carbenes</subject><subject>Organic chemistry</subject><subject>organocatalysis</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><recordid>eNqFkctOJCEUhonReJ2tS1OJm9l0C1QVyMakrbSjiZeFmsyOnKKgxdCg0D2mdj7CPOM8yWBa28vGFSfwnS-c8yO0S_CQYEwPVEpqSDERmJYVW0Gb5JBVg5pVv1eXdUk20FZK9xgzLBhbRxsl4bxilG-i8eW_57-neqZjUL1yVhUNxFZ7XYxU74qRt8EXV3ECPiiYgeuTTUXbF8fgXO68sM5ZP9lBawZc0j9ez210ezK-aU4H51e_zprR-UDVuGYDVnedAUYMAdNpJoxRnCrWCgDV4q4CAYyCoHUNitecEGVanu9aQ7AAUpbb6GjhfZi3U90p7WcRnHyIdgqxlwGs_Pzi7Z2chD-SCU45o1nw81UQw-Ncp5mc2qS0c-B1mCdJSyKIqPI-M7r_Bb0P8-jzeJkqK0JrjKtMDReUiiGlqM3yMwTLl4TkS0JymVBu2Ps4whJ_iyQDYgE8Waf7b3Syub5u3uX_AWXroGg</recordid><startdate>20200109</startdate><enddate>20200109</enddate><creator>Nicholson, William I.</creator><creator>Seastram, Alex C.</creator><creator>Iqbal, Saqib A.</creator><creator>Reed‐Berendt, Benjamin G.</creator><creator>Morrill, Louis C.</creator><creator>Browne, Duncan L.</creator><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons 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><scope>5PM</scope></search><sort><creationdate>20200109</creationdate><title>N‐Heterocyclic Carbene Acyl Anion Organocatalysis by Ball‐Milling</title><author>Nicholson, William I. ; Seastram, Alex C. ; Iqbal, Saqib A. ; Reed‐Berendt, Benjamin G. ; Morrill, Louis C. ; Browne, Duncan L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5056-65ddfa61f1afde69ffc72c6b9aacb0d4a9a62a9255ac75711cfb79a6bf109a133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>acyl anion</topic><topic>Anions</topic><topic>ball milling</topic><topic>Benzoin</topic><topic>Communication</topic><topic>Communications</topic><topic>mechanochemistry</topic><topic>N-heterocyclic carbenes</topic><topic>Organic chemistry</topic><topic>organocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nicholson, William I.</creatorcontrib><creatorcontrib>Seastram, Alex C.</creatorcontrib><creatorcontrib>Iqbal, Saqib A.</creatorcontrib><creatorcontrib>Reed‐Berendt, Benjamin G.</creatorcontrib><creatorcontrib>Morrill, Louis C.</creatorcontrib><creatorcontrib>Browne, Duncan L.</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><collection>PubMed Central (Full Participant titles)</collection><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nicholson, William I.</au><au>Seastram, Alex C.</au><au>Iqbal, Saqib A.</au><au>Reed‐Berendt, Benjamin G.</au><au>Morrill, Louis C.</au><au>Browne, Duncan L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N‐Heterocyclic Carbene Acyl Anion Organocatalysis by Ball‐Milling</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2020-01-09</date><risdate>2020</risdate><volume>13</volume><issue>1</issue><spage>131</spage><epage>135</epage><pages>131-135</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>The ability to conduct N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent‐minimised conditions.
Having a ball: The ability to conduct mechanistically complex N‐heterocyclic carbene‐catalysed acyl anion chemistry under ball‐milling conditions is reported for the first time. This process is exemplified through applications to intermolecular‐benzoin, intramolecular‐benzoin, intermolecular‐Stetter and intramolecular‐Stetter reactions including asymmetric examples.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31774627</pmid><doi>10.1002/cssc.201902346</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| issn | 1864-5631 1864-564X |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | acyl anion Anions ball milling Benzoin Communication Communications mechanochemistry N-heterocyclic carbenes Organic chemistry organocatalysis |
| title | N‐Heterocyclic Carbene Acyl Anion Organocatalysis by Ball‐Milling |
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