Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans
A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs 2 CO 3 promoted C-C σ-bond activation of α-aryl ketones followed by Zn-catalyzed intramolecular cyclization. This represents the first exampl...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2019-03, Vol.17 (1), p.2725-2733 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Yuan, Yang Tan, Hailu Kong, Lingkai Zheng, Zhong Xu, Murong Huang, Jiaqi Li, Yanzhong |
| description | A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs
2
CO
3
promoted C-C σ-bond activation of α-aryl ketones followed by Zn-catalyzed intramolecular cyclization. This represents the first example for the preparation of tetrasubstituted furans through rearrangement of molecular skeletons and subsequent transformations. Mild reaction conditions and readily accessible starting materials make the protocol attractive in organic synthesis.
Atom-economical synthesis of tetrasubstituted furans from α-aryl ketones and alkynones through base-promoted cleavage of unstrained C-C single bonds of ketones and subsequent Zn-catalyzed cyclization. |
| doi_str_mv | 10.1039/c9ob00081j |
| format | Article |
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2
CO
3
promoted C-C σ-bond activation of α-aryl ketones followed by Zn-catalyzed intramolecular cyclization. This represents the first example for the preparation of tetrasubstituted furans through rearrangement of molecular skeletons and subsequent transformations. Mild reaction conditions and readily accessible starting materials make the protocol attractive in organic synthesis.
Atom-economical synthesis of tetrasubstituted furans from α-aryl ketones and alkynones through base-promoted cleavage of unstrained C-C single bonds of ketones and subsequent Zn-catalyzed cyclization.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob00081j</identifier><identifier>PMID: 30775765</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Activation ; Aromatic compounds ; Cascade chemical reactions ; Chemical synthesis ; Furans ; Ketones ; Pesticides ; Transition metals ; Zinc</subject><ispartof>Organic & biomolecular chemistry, 2019-03, Vol.17 (1), p.2725-2733</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-6b3b1d10cb57aa5a69bf0af35150c6d0e12df321bfcfb3933f82fd4dadaa58a23</citedby><cites>FETCH-LOGICAL-c363t-6b3b1d10cb57aa5a69bf0af35150c6d0e12df321bfcfb3933f82fd4dadaa58a23</cites><orcidid>0000-0002-7028-3646 ; 0000-0002-2898-3075 ; 0000-0001-7363-8222 ; 0000-0002-3868-006X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30775765$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yuan, Yang</creatorcontrib><creatorcontrib>Tan, Hailu</creatorcontrib><creatorcontrib>Kong, Lingkai</creatorcontrib><creatorcontrib>Zheng, Zhong</creatorcontrib><creatorcontrib>Xu, Murong</creatorcontrib><creatorcontrib>Huang, Jiaqi</creatorcontrib><creatorcontrib>Li, Yanzhong</creatorcontrib><title>Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs
2
CO
3
promoted C-C σ-bond activation of α-aryl ketones followed by Zn-catalyzed intramolecular cyclization. This represents the first example for the preparation of tetrasubstituted furans through rearrangement of molecular skeletons and subsequent transformations. Mild reaction conditions and readily accessible starting materials make the protocol attractive in organic synthesis.
Atom-economical synthesis of tetrasubstituted furans from α-aryl ketones and alkynones through base-promoted cleavage of unstrained C-C single bonds of ketones and subsequent Zn-catalyzed cyclization.</description><subject>Activation</subject><subject>Aromatic compounds</subject><subject>Cascade chemical reactions</subject><subject>Chemical synthesis</subject><subject>Furans</subject><subject>Ketones</subject><subject>Pesticides</subject><subject>Transition metals</subject><subject>Zinc</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp90ctOFTEcBvCGaACPbthrStgQk0o7nc6FnUzES0jYwMbNpNfQ40x7aDsmh62v4Uv4IvJKdDh4TFy4apP--qX_fgAcEPyOYNqeyNYLjHFDljtgn5R1jTCj7bPtvsB74EWMS4xJW1flLtijuK5ZXbF98PMqcBdtst6hUSc-IBO0hh3q4P0PJLxTkMtkv_NZQG_g71-Ih_UAv-nknY6QZxEnEfXtpF2CXx2SPMes77SC1qXARz9oOQ08QLmWg717TDqFce3SjY42zqFJZzinJJumlG-aaX7WS_Dc8CHqV0_rAlyff7jqPqGLy4-fu_cXSNKKJlQJKogiWApWc8541QqDuaGMMCwrhTUplKEFEUYaQVtKTVMYVSqusm54QRfgeJO7Cj6PEVM_2ij1MHCn_RT7gjSUNCVlLNOjf-jST8Hl182qKcuSFrN6u1Ey-BiDNv0q2DH_W09wP3fWd-3l2WNnXzJ-8xQ5iVGrLf1TUgaHGxCi3J7-Lb1f5ekW4PX_DH0AL0SseA</recordid><startdate>20190306</startdate><enddate>20190306</enddate><creator>Yuan, Yang</creator><creator>Tan, Hailu</creator><creator>Kong, Lingkai</creator><creator>Zheng, Zhong</creator><creator>Xu, Murong</creator><creator>Huang, Jiaqi</creator><creator>Li, Yanzhong</creator><general>Royal Society of Chemistry</general><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/0000-0002-7028-3646</orcidid><orcidid>https://orcid.org/0000-0002-2898-3075</orcidid><orcidid>https://orcid.org/0000-0001-7363-8222</orcidid><orcidid>https://orcid.org/0000-0002-3868-006X</orcidid></search><sort><creationdate>20190306</creationdate><title>Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans</title><author>Yuan, Yang ; Tan, Hailu ; Kong, Lingkai ; Zheng, Zhong ; Xu, Murong ; Huang, Jiaqi ; Li, Yanzhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-6b3b1d10cb57aa5a69bf0af35150c6d0e12df321bfcfb3933f82fd4dadaa58a23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Activation</topic><topic>Aromatic compounds</topic><topic>Cascade chemical reactions</topic><topic>Chemical synthesis</topic><topic>Furans</topic><topic>Ketones</topic><topic>Pesticides</topic><topic>Transition metals</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yuan, Yang</creatorcontrib><creatorcontrib>Tan, Hailu</creatorcontrib><creatorcontrib>Kong, Lingkai</creatorcontrib><creatorcontrib>Zheng, Zhong</creatorcontrib><creatorcontrib>Xu, Murong</creatorcontrib><creatorcontrib>Huang, Jiaqi</creatorcontrib><creatorcontrib>Li, Yanzhong</creatorcontrib><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>Yuan, Yang</au><au>Tan, Hailu</au><au>Kong, Lingkai</au><au>Zheng, Zhong</au><au>Xu, Murong</au><au>Huang, Jiaqi</au><au>Li, Yanzhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2019-03-06</date><risdate>2019</risdate><volume>17</volume><issue>1</issue><spage>2725</spage><epage>2733</epage><pages>2725-2733</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs
2
CO
3
promoted C-C σ-bond activation of α-aryl ketones followed by Zn-catalyzed intramolecular cyclization. This represents the first example for the preparation of tetrasubstituted furans through rearrangement of molecular skeletons and subsequent transformations. Mild reaction conditions and readily accessible starting materials make the protocol attractive in organic synthesis.
Atom-economical synthesis of tetrasubstituted furans from α-aryl ketones and alkynones through base-promoted cleavage of unstrained C-C single bonds of ketones and subsequent Zn-catalyzed cyclization.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30775765</pmid><doi>10.1039/c9ob00081j</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-7028-3646</orcidid><orcidid>https://orcid.org/0000-0002-2898-3075</orcidid><orcidid>https://orcid.org/0000-0001-7363-8222</orcidid><orcidid>https://orcid.org/0000-0002-3868-006X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2019-03, Vol.17 (1), p.2725-2733 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_journals_2188444325 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Activation Aromatic compounds Cascade chemical reactions Chemical synthesis Furans Ketones Pesticides Transition metals Zinc |
| title | Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans |
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