Pd‐Catalyzed, Ligand‐Enabled Stereoselective 1,2‐Iodine(III) Shift/1,1‐Carboxyalkynylation of Alkynylbenziodoxoles
A PdII‐catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk‐1‐en‐3‐ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by ste...
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| Veröffentlicht in: | Chemistry : a European journal 2017-01, Vol.23 (7), p.1521-1525 |
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| creator | Wu, Junliang Xu, Kai Hirao, Hajime Yoshikai, Naohiko |
| description | A PdII‐catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk‐1‐en‐3‐ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations.
Shifty iodine: A PdII‐octahydrophenazine catalyst promotes 2:1 coupling of alkynylbenziodoxole with carboxylic acid. The reaction involves a PdII‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations. |
| doi_str_mv | 10.1002/chem.201605772 |
| format | Article |
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Shifty iodine: A PdII‐octahydrophenazine catalyst promotes 2:1 coupling of alkynylbenziodoxole with carboxylic acid. The reaction involves a PdII‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201605772</identifier><identifier>PMID: 27966272</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>alkynylation ; carboxylic acid ; Carboxylic acids ; Catalysts ; Chemical reactions ; Chemistry ; Coupling ; cross-coupling ; hypervalent iodine ; Iodine ; Ligands ; palladium ; Transformations</subject><ispartof>Chemistry : a European journal, 2017-01, Vol.23 (7), p.1521-1525</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5092-de0183704bafa0975337213ae4e8e2f7f55242a0904eae2c8c7a8b7f8ee9805f3</citedby><cites>FETCH-LOGICAL-c5092-de0183704bafa0975337213ae4e8e2f7f55242a0904eae2c8c7a8b7f8ee9805f3</cites><orcidid>0000-0002-8997-3268</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.201605772$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201605772$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27966272$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Junliang</creatorcontrib><creatorcontrib>Xu, Kai</creatorcontrib><creatorcontrib>Hirao, Hajime</creatorcontrib><creatorcontrib>Yoshikai, Naohiko</creatorcontrib><title>Pd‐Catalyzed, Ligand‐Enabled Stereoselective 1,2‐Iodine(III) Shift/1,1‐Carboxyalkynylation of Alkynylbenziodoxoles</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A PdII‐catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk‐1‐en‐3‐ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations.
Shifty iodine: A PdII‐octahydrophenazine catalyst promotes 2:1 coupling of alkynylbenziodoxole with carboxylic acid. The reaction involves a PdII‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations.</description><subject>alkynylation</subject><subject>carboxylic acid</subject><subject>Carboxylic acids</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Coupling</subject><subject>cross-coupling</subject><subject>hypervalent iodine</subject><subject>Iodine</subject><subject>Ligands</subject><subject>palladium</subject><subject>Transformations</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkcFu1DAQhq0KRJeWa48oEpcibbZjO47tY7Xa0kiLQGp7jpxkTF28cYmzbbMnHoFn5EnIsqVIXOhpNDPffNLoJ-SIwowCsJP6GlczBjQHISXbIxMqGE25zMULMgGdyTQXXO-T1zHeAIDOOX9F9pnUec4km5DN5-bn9x9z0xs_bLCZJkv3xbTb2aI1lccmueixwxDRY927O0zolI3bIjSuxeOiKN4nF9fO9id0Sn-buio8DMZ_HdrBm96FNgk2Od31FbYbF5rwEDzGQ_LSGh_xzWM9IFdni8v5ebr89KGYny7TWoBmaYNAFZeQVcYa0FJwLhnlBjNUyKy0QrCMjRvI0CCrVS2NqqRViFqBsPyAHO-8t134tsbYlysXa_TetBjWsaRKZRQop_QZqGC5VJKrEX33D3oT1l07PjJSOWfABdUjNdtRdRdi7NCWt51bmW4oKZTbAMttgOVTgOPB20ftulph84T_SWwE9A64dx6H_-jK-fni41_5L6EQqmc</recordid><startdate>20170131</startdate><enddate>20170131</enddate><creator>Wu, Junliang</creator><creator>Xu, Kai</creator><creator>Hirao, Hajime</creator><creator>Yoshikai, Naohiko</creator><general>Wiley Subscription Services, Inc</general><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><orcidid>https://orcid.org/0000-0002-8997-3268</orcidid></search><sort><creationdate>20170131</creationdate><title>Pd‐Catalyzed, Ligand‐Enabled Stereoselective 1,2‐Iodine(III) Shift/1,1‐Carboxyalkynylation of Alkynylbenziodoxoles</title><author>Wu, Junliang ; Xu, Kai ; Hirao, Hajime ; Yoshikai, Naohiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5092-de0183704bafa0975337213ae4e8e2f7f55242a0904eae2c8c7a8b7f8ee9805f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>alkynylation</topic><topic>carboxylic acid</topic><topic>Carboxylic acids</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Coupling</topic><topic>cross-coupling</topic><topic>hypervalent iodine</topic><topic>Iodine</topic><topic>Ligands</topic><topic>palladium</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Junliang</creatorcontrib><creatorcontrib>Xu, Kai</creatorcontrib><creatorcontrib>Hirao, Hajime</creatorcontrib><creatorcontrib>Yoshikai, Naohiko</creatorcontrib><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><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Junliang</au><au>Xu, Kai</au><au>Hirao, Hajime</au><au>Yoshikai, Naohiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pd‐Catalyzed, Ligand‐Enabled Stereoselective 1,2‐Iodine(III) Shift/1,1‐Carboxyalkynylation of Alkynylbenziodoxoles</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-01-31</date><risdate>2017</risdate><volume>23</volume><issue>7</issue><spage>1521</spage><epage>1525</epage><pages>1521-1525</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A PdII‐catalyzed 2:1 coupling reaction of alkynylbenziodoxole with carboxylic acid to afford (alk‐1‐en‐3‐ynyl)benziodoxole, which is efficiently promoted by an octahydrophenazine ligand, is reported. The reaction involves a Pd‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups (the latter originating from another molecule of the alkynylbenziodoxole) into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations.
Shifty iodine: A PdII‐octahydrophenazine catalyst promotes 2:1 coupling of alkynylbenziodoxole with carboxylic acid. The reaction involves a PdII‐assisted 1,2‐iodine(III) shift of the alkynylbenziodoxole followed by stereoselective introduction of carboxy and alkynyl groups into the 1‐position of the transient Pd‐vinylidene species. The product of this 1,1‐carboxyalkynylation reaction serves as a new functionalized enyne‐type building block for further synthetic transformations.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>27966272</pmid><doi>10.1002/chem.201605772</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-8997-3268</orcidid></addata></record> |
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| subjects | alkynylation carboxylic acid Carboxylic acids Catalysts Chemical reactions Chemistry Coupling cross-coupling hypervalent iodine Iodine Ligands palladium Transformations |
| title | Pd‐Catalyzed, Ligand‐Enabled Stereoselective 1,2‐Iodine(III) Shift/1,1‐Carboxyalkynylation of Alkynylbenziodoxoles |
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