Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines
A copper catalyzed annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C-F bond cleavages has been developed. In this approach, the annulation occurred between the in situ formed dienes from trifluorometh...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2022-05, Vol.2 (18), p.3731-3736 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Fu, Yiwei Shi, Haoyu Lei, Shengshu Shi, Lei Li, Hao |
| description | A copper catalyzed annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C-F bond cleavages has been developed. In this approach, the annulation occurred between the
in situ
formed dienes from trifluoromethyl ketimines
via
the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C-F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.
A copper catalyzed [4 + 2]annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones has been developed for the synthesis of 3-fluoropyridines in moderate yields through double C-F bond cleavages. |
| doi_str_mv | 10.1039/d2ob00133k |
| format | Article |
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in situ
formed dienes from trifluoromethyl ketimines
via
the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C-F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.
A copper catalyzed [4 + 2]annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones has been developed for the synthesis of 3-fluoropyridines in moderate yields through double C-F bond cleavages.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob00133k</identifier><identifier>PMID: 35467681</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Catalysis ; Chemical reactions ; Cleavage ; Copper ; Copper - chemistry ; Cycloaddition ; Cycloaddition Reaction ; Dienes ; Imines ; Molecular Structure ; Organic chemistry ; Substitutes</subject><ispartof>Organic & biomolecular chemistry, 2022-05, Vol.2 (18), p.3731-3736</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c252t-5d5b6a9dea57bd6a1b7168203f69acc704854d5a922f370060de9a47f6e2d6ff3</citedby><cites>FETCH-LOGICAL-c252t-5d5b6a9dea57bd6a1b7168203f69acc704854d5a922f370060de9a47f6e2d6ff3</cites><orcidid>0000-0002-8978-0247</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27928,27929</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35467681$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fu, Yiwei</creatorcontrib><creatorcontrib>Shi, Haoyu</creatorcontrib><creatorcontrib>Lei, Shengshu</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><creatorcontrib>Li, Hao</creatorcontrib><title>Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A copper catalyzed annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C-F bond cleavages has been developed. In this approach, the annulation occurred between the
in situ
formed dienes from trifluoromethyl ketimines
via
the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C-F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.
A copper catalyzed [4 + 2]annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones has been developed for the synthesis of 3-fluoropyridines in moderate yields through double C-F bond cleavages.</description><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Cleavage</subject><subject>Copper</subject><subject>Copper - chemistry</subject><subject>Cycloaddition</subject><subject>Cycloaddition Reaction</subject><subject>Dienes</subject><subject>Imines</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Substitutes</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0ctP3DAQB2CrKiqP9tI7yFIvCBTw2_GxLE-BxKWcAEWOH6xpNl7s5JD-9TVdukicxtJ8Ho1-A8B3jI4wourYktgihCn9_QlsYSZlhThVn9dvgjbBds7PxSgp2BewSTkTUtR4CzzMRmj0oLvpj7PwnsFDSB6hmUwXtbVhCLGHPiY4zB3MU19KDhlGD-fhad5NMI9tHsIwDuU3rXw3xhSXUwo29C5_BRted9l9e6s74O787Nfssrq5vbia_bypDOFkqLjlrdDKOs1la4XGrcSiJoh6obQxErGaM8u1IsRTiZBA1inNpBeOWOE93QH7q7nLFF9Gl4dmEbJxXad7F8fcEME5RkgpVeiPD_Q5jqkv2xUlcF1LxmhRBytlUsw5Od8sU1joNDUYNa-ZN6fk9uRf5tcF772NHNuFs2v6P-QCdlcgZbPuvh-N_gVF-oVb</recordid><startdate>20220511</startdate><enddate>20220511</enddate><creator>Fu, Yiwei</creator><creator>Shi, Haoyu</creator><creator>Lei, Shengshu</creator><creator>Shi, Lei</creator><creator>Li, Hao</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</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/0000-0002-8978-0247</orcidid></search><sort><creationdate>20220511</creationdate><title>Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines</title><author>Fu, Yiwei ; Shi, Haoyu ; Lei, Shengshu ; Shi, Lei ; Li, Hao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c252t-5d5b6a9dea57bd6a1b7168203f69acc704854d5a922f370060de9a47f6e2d6ff3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Cleavage</topic><topic>Copper</topic><topic>Copper - chemistry</topic><topic>Cycloaddition</topic><topic>Cycloaddition Reaction</topic><topic>Dienes</topic><topic>Imines</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fu, Yiwei</creatorcontrib><creatorcontrib>Shi, Haoyu</creatorcontrib><creatorcontrib>Lei, Shengshu</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><creatorcontrib>Li, Hao</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</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>Fu, Yiwei</au><au>Shi, Haoyu</au><au>Lei, Shengshu</au><au>Shi, Lei</au><au>Li, Hao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2022-05-11</date><risdate>2022</risdate><volume>2</volume><issue>18</issue><spage>3731</spage><epage>3736</epage><pages>3731-3736</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A copper catalyzed annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C-F bond cleavages has been developed. In this approach, the annulation occurred between the
in situ
formed dienes from trifluoromethyl ketimines
via
the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C-F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.
A copper catalyzed [4 + 2]annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones has been developed for the synthesis of 3-fluoropyridines in moderate yields through double C-F bond cleavages.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35467681</pmid><doi>10.1039/d2ob00133k</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8978-0247</orcidid></addata></record> |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Catalysis Chemical reactions Cleavage Copper Copper - chemistry Cycloaddition Cycloaddition Reaction Dienes Imines Molecular Structure Organic chemistry Substitutes |
| title | Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines |
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