Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion
Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2021-08, Vol.19 (31), p.6786-6791 |
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| container_issue | 31 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Clarke, Joshua J Devaraj, Karthik Bestvater, Brian P Kojima, Ryoto Eisenberger, Patrick DeJesus, Joseph F Crudden, Cathleen M |
| description | Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4-hydrosilylquinoline product selectively which can be further functionalized in a one-pot synthesis to give unique γ-amino alcohol derivatives. Control experiments suggest that the borenium ion catalyzes both the hydrosilylation and subsequent addition to the aldehyde.
Aldimines and ketimines are hydrosilylated with borenium catalysts at room temperature, giving the corresponding amines in excellent yields. For quinolines, subsequent Mukaiyama aldol reactions can be performed, which are also borenium-ion catalyzed. |
| doi_str_mv | 10.1039/d1ob01056e |
| format | Article |
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Aldimines and ketimines are hydrosilylated with borenium catalysts at room temperature, giving the corresponding amines in excellent yields. For quinolines, subsequent Mukaiyama aldol reactions can be performed, which are also borenium-ion catalyzed.</description><subject>Aldehydes</subject><subject>Amines</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Crystallography</subject><subject>Hydrosilylation</subject><subject>Imines</subject><subject>Organic compounds</subject><subject>Physical Sciences</subject><subject>Quinolines</subject><subject>Room temperature</subject><subject>Science & Technology</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqN0k-P1SAQAPDGaNw_evFuQuLFaKpDKaUc9bm6Jmv2oudmSqeRlcJbaLOpH8TPK_aZZ7InTxD4zQAzFMUzDm84CP124KEHDrKhB8Upr5UqQQr98Div4KQ4S-kGgGvV1I-LE1EL3raiPi1-Xa5DDMm61eFsg2foB_Zl-YF2xQkZuiG4cl73xCKh2UQY2e1ifXDWU9r893s5srDTtmtwRrf-pIH1K0M2UQoZWJM3Yk-eyjRjb53dRIjk7TKxLJ4Uj0Z0iZ7-Hc-Lbx8vvu4uy6vrT593765KI6Scy_wEKSopADmgVjWvBYwaBJIaGhjJcICmMUC9kmCwHVtdV9hr1eYVUXNxXrw85N3HcLtQmrvJJkPOoaewpK6SUuqm5W2T6Yt79CYs0efbZdXkc3Ql2qxeHZTJFUmRxm4f7YRx7Th0f7rVfeDX77duXWTcHvAd9WFMxpI3dAyAnFMpJWuZZ8B3dt6quwuLn3Po6_8Pzfr5QcdkjujftxG_AYGbslU</recordid><startdate>20210821</startdate><enddate>20210821</enddate><creator>Clarke, Joshua J</creator><creator>Devaraj, Karthik</creator><creator>Bestvater, Brian P</creator><creator>Kojima, Ryoto</creator><creator>Eisenberger, Patrick</creator><creator>DeJesus, Joseph F</creator><creator>Crudden, Cathleen M</creator><general>Royal Soc Chemistry</general><general>Royal Society of Chemistry</general><scope>1KM</scope><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3857-5008</orcidid><orcidid>https://orcid.org/0000-0003-2154-8107</orcidid></search><sort><creationdate>20210821</creationdate><title>Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion</title><author>Clarke, Joshua J ; Devaraj, Karthik ; Bestvater, Brian P ; Kojima, Ryoto ; Eisenberger, Patrick ; DeJesus, Joseph F ; Crudden, Cathleen M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-834532530a10a9741430f903ae7d60fec10066c0eb750ca8f8942ab978eb73413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aldehydes</topic><topic>Amines</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Crystallography</topic><topic>Hydrosilylation</topic><topic>Imines</topic><topic>Organic compounds</topic><topic>Physical Sciences</topic><topic>Quinolines</topic><topic>Room temperature</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Clarke, Joshua J</creatorcontrib><creatorcontrib>Devaraj, Karthik</creatorcontrib><creatorcontrib>Bestvater, Brian P</creatorcontrib><creatorcontrib>Kojima, Ryoto</creatorcontrib><creatorcontrib>Eisenberger, Patrick</creatorcontrib><creatorcontrib>DeJesus, Joseph F</creatorcontrib><creatorcontrib>Crudden, Cathleen M</creatorcontrib><collection>Index Chemicus</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Clarke, Joshua J</au><au>Devaraj, Karthik</au><au>Bestvater, Brian P</au><au>Kojima, Ryoto</au><au>Eisenberger, Patrick</au><au>DeJesus, Joseph F</au><au>Crudden, Cathleen M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion</atitle><jtitle>Organic & biomolecular chemistry</jtitle><stitle>ORG BIOMOL CHEM</stitle><date>2021-08-21</date><risdate>2021</risdate><volume>19</volume><issue>31</issue><spage>6786</spage><epage>6791</epage><pages>6786-6791</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Aldimines and ketimines containing electron-donating and electron-withdrawing groups can be hydrosilylated with borenium catalysts at as low as 1 mol% catalyst loading at room temperature, providing the corresponding secondary amines in excellent yields. Reactions with 2-phenylquinoline gave the 1,4-hydrosilylquinoline product selectively which can be further functionalized in a one-pot synthesis to give unique γ-amino alcohol derivatives. Control experiments suggest that the borenium ion catalyzes both the hydrosilylation and subsequent addition to the aldehyde.
Aldimines and ketimines are hydrosilylated with borenium catalysts at room temperature, giving the corresponding amines in excellent yields. For quinolines, subsequent Mukaiyama aldol reactions can be performed, which are also borenium-ion catalyzed.</abstract><cop>CAMBRIDGE</cop><pub>Royal Soc Chemistry</pub><pmid>34318834</pmid><doi>10.1039/d1ob01056e</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3857-5008</orcidid><orcidid>https://orcid.org/0000-0003-2154-8107</orcidid></addata></record> |
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| subjects | Aldehydes Amines Catalysts Chemistry Chemistry, Organic Crystallography Hydrosilylation Imines Organic compounds Physical Sciences Quinolines Room temperature Science & Technology |
| title | Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion |
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