Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)H Functionalization
A rhodium(III)‐catalyzed [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with internal alkynes is presented. This transformation provides straightforward access to indeno[1,7‐cd]azepine architectures through a sequence involving the formation of a rhodium(III) azavinyl carbene, dual C(sp2)...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-05, Vol.54 (22), p.6595-6599 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Yang, Yuan Zhou, Ming-Bo Ouyang, Xuan-Hui Pi, Rui Song, Ren-Jie Li, Jin-Heng |
| description | A rhodium(III)‐catalyzed [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with internal alkynes is presented. This transformation provides straightforward access to indeno[1,7‐cd]azepine architectures through a sequence involving the formation of a rhodium(III) azavinyl carbene, dual C(sp2)H functionalization, and [3+2]/[5+2] annulation.
A quantum leap in complexity: A general strategy based on rhodium(III) azavinyl carbene intermediates was established for the oxidative [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with alkynes. This general method provided densely functionalized indeno[1,7‐cd]azepine architectures with excellent selectivity through the functionalization of two C(sp2)H bonds (see scheme; Cp*=pentamethylcyclopentadienyl, Ts= p‐toluenesulfonyl). |
| doi_str_mv | 10.1002/anie.201501260 |
| format | Article |
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A quantum leap in complexity: A general strategy based on rhodium(III) azavinyl carbene intermediates was established for the oxidative [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with alkynes. This general method provided densely functionalized indeno[1,7‐cd]azepine architectures with excellent selectivity through the functionalization of two C(sp2)H bonds (see scheme; Cp*=pentamethylcyclopentadienyl, Ts= p‐toluenesulfonyl).</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201501260</identifier><identifier>PMID: 25872912</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>7-cd]azepines ; alkynes ; Alkynes - chemistry ; annulation ; Azepines - chemistry ; Carbon - chemistry ; Catalysis ; Cycloaddition Reaction ; Hydrogen - chemistry ; indeno ; indeno[1,7‐cd]azepines ; rhodium ; Rhodium - chemistry ; triazoles ; Triazoles - chemistry</subject><ispartof>Angewandte Chemie International Edition, 2015-05, Vol.54 (22), p.6595-6599</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5180-682afe0fe8498cbec811c85ce177a47519235c0825141bfcc1a7e92ea85c39f73</citedby><cites>FETCH-LOGICAL-c5180-682afe0fe8498cbec811c85ce177a47519235c0825141bfcc1a7e92ea85c39f73</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%2Fanie.201501260$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201501260$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25872912$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Yuan</creatorcontrib><creatorcontrib>Zhou, Ming-Bo</creatorcontrib><creatorcontrib>Ouyang, Xuan-Hui</creatorcontrib><creatorcontrib>Pi, Rui</creatorcontrib><creatorcontrib>Song, Ren-Jie</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><title>Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)H Functionalization</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A rhodium(III)‐catalyzed [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with internal alkynes is presented. This transformation provides straightforward access to indeno[1,7‐cd]azepine architectures through a sequence involving the formation of a rhodium(III) azavinyl carbene, dual C(sp2)H functionalization, and [3+2]/[5+2] annulation.
A quantum leap in complexity: A general strategy based on rhodium(III) azavinyl carbene intermediates was established for the oxidative [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with alkynes. This general method provided densely functionalized indeno[1,7‐cd]azepine architectures with excellent selectivity through the functionalization of two C(sp2)H bonds (see scheme; Cp*=pentamethylcyclopentadienyl, Ts= p‐toluenesulfonyl).</description><subject>7-cd]azepines</subject><subject>alkynes</subject><subject>Alkynes - chemistry</subject><subject>annulation</subject><subject>Azepines - chemistry</subject><subject>Carbon - chemistry</subject><subject>Catalysis</subject><subject>Cycloaddition Reaction</subject><subject>Hydrogen - chemistry</subject><subject>indeno</subject><subject>indeno[1,7‐cd]azepines</subject><subject>rhodium</subject><subject>Rhodium - chemistry</subject><subject>triazoles</subject><subject>Triazoles - chemistry</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctu1DAUhiNERUthyxJFYjMVzdTHjmNnGQ29RBoNFxVYVMjyeBzGrSeZ2olK5gX6IDwIj8Qr4CFlhNiw8bGOvv-Tjv4oegFoDAjhE1kbPcYIKAKcoUfRAVAMCWGMPA7_lJCEcQr70VPvrwPPOcqeRPuYcoZzwAfR_YdlszDdalSW5VEyka20_UYv4ivyGn85uaLhjYu67qxsTVPHTRWnSeF6G8MxPibJpTNy01jt4zvTLuOybrWrpY0Le9PXYdsuXdN9XcZvurCcjPwaH_38_uMiPutqtRVKaza_zc-ivUpar58_zMPo49np5eQimb49LyfFNFEUOEoyjmWlUaV5mnM114oDKE6VBsZkyijkmFCFOKaQwrxSCiTTOdYyMCSvGDmMRoN37ZrbTvtWrIxX2lpZ66bzAjJOGE0RJwF99Q963XTb6wYKSIZTCNR4oJRrvHe6EmtnVtL1ApDYViS2FYldRSHw8kHbzVd6scP_dBKAfADujNX9f3SimJWnf8uTIWt8q7_tstLdiIyFw8Tn2bmYIngP72afREZ-ARuXqrY</recordid><startdate>20150526</startdate><enddate>20150526</enddate><creator>Yang, Yuan</creator><creator>Zhou, Ming-Bo</creator><creator>Ouyang, Xuan-Hui</creator><creator>Pi, Rui</creator><creator>Song, Ren-Jie</creator><creator>Li, Jin-Heng</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20150526</creationdate><title>Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)H Functionalization</title><author>Yang, Yuan ; Zhou, Ming-Bo ; Ouyang, Xuan-Hui ; Pi, Rui ; Song, Ren-Jie ; Li, Jin-Heng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5180-682afe0fe8498cbec811c85ce177a47519235c0825141bfcc1a7e92ea85c39f73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>7-cd]azepines</topic><topic>alkynes</topic><topic>Alkynes - chemistry</topic><topic>annulation</topic><topic>Azepines - chemistry</topic><topic>Carbon - chemistry</topic><topic>Catalysis</topic><topic>Cycloaddition Reaction</topic><topic>Hydrogen - chemistry</topic><topic>indeno</topic><topic>indeno[1,7‐cd]azepines</topic><topic>rhodium</topic><topic>Rhodium - chemistry</topic><topic>triazoles</topic><topic>Triazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Yuan</creatorcontrib><creatorcontrib>Zhou, Ming-Bo</creatorcontrib><creatorcontrib>Ouyang, Xuan-Hui</creatorcontrib><creatorcontrib>Pi, Rui</creatorcontrib><creatorcontrib>Song, Ren-Jie</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Yuan</au><au>Zhou, Ming-Bo</au><au>Ouyang, Xuan-Hui</au><au>Pi, Rui</au><au>Song, Ren-Jie</au><au>Li, Jin-Heng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)H Functionalization</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-05-26</date><risdate>2015</risdate><volume>54</volume><issue>22</issue><spage>6595</spage><epage>6599</epage><pages>6595-6599</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A rhodium(III)‐catalyzed [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with internal alkynes is presented. This transformation provides straightforward access to indeno[1,7‐cd]azepine architectures through a sequence involving the formation of a rhodium(III) azavinyl carbene, dual C(sp2)H functionalization, and [3+2]/[5+2] annulation.
A quantum leap in complexity: A general strategy based on rhodium(III) azavinyl carbene intermediates was established for the oxidative [3+2]/[5+2] annulation of 4‐aryl 1‐tosyl‐1,2,3‐triazoles with alkynes. This general method provided densely functionalized indeno[1,7‐cd]azepine architectures with excellent selectivity through the functionalization of two C(sp2)H bonds (see scheme; Cp*=pentamethylcyclopentadienyl, Ts= p‐toluenesulfonyl).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25872912</pmid><doi>10.1002/anie.201501260</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | 7-cd]azepines alkynes Alkynes - chemistry annulation Azepines - chemistry Carbon - chemistry Catalysis Cycloaddition Reaction Hydrogen - chemistry indeno indeno[1,7‐cd]azepines rhodium Rhodium - chemistry triazoles Triazoles - chemistry |
| title | Rhodium(III)-Catalyzed [3+2]/[5+2] Annulation of 4-Aryl 1,2,3-Triazoles with Internal Alkynes through Dual C(sp2)H Functionalization |
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