Palladium‐Catalyzed Spirocyclization through C−H Activation and Regioselective Alkyne Insertion
A Pd‐catalyzed spirocyclization involving a sequential carbopalladation, intramolecular C−H activation, and a highly regioselective alkyne insertion to afford spirooxindoles and spirodihydrobenzofurans has been achieved. The spirocyclic products were generated in good to excellent yields with comple...
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| Veröffentlicht in: | Angewandte Chemie 2017-08, Vol.129 (36), p.11060-11063 |
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| container_end_page | 11063 |
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| container_issue | 36 |
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| container_title | Angewandte Chemie |
| container_volume | 129 |
| creator | Yoon, Hyung Rölz, Martin Landau, Felicitas Lautens, Mark |
| description | A Pd‐catalyzed spirocyclization involving a sequential carbopalladation, intramolecular C−H activation, and a highly regioselective alkyne insertion to afford spirooxindoles and spirodihydrobenzofurans has been achieved. The spirocyclic products were generated in good to excellent yields with complete regiocontrol in a readily scalable procedure.
Punktgenau verknüpft: Eine Pd‐katalysierte Reaktionskaskade aus sequenzieller Carbopalladierung, intramolekularer C‐H‐Aktivierung und hoch regioselektiver Alkininsertion erzeugt ein breites Spektrum an Spirooxindolen und Spirodihydrobenzofuranen. Die Spirocyclen werden in guten bis hervorragenden Ausbeuten und mit Regioisomerenverhältnissen >20:1 erhalten. |
| doi_str_mv | 10.1002/ange.201706325 |
| format | Article |
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Punktgenau verknüpft: Eine Pd‐katalysierte Reaktionskaskade aus sequenzieller Carbopalladierung, intramolekularer C‐H‐Aktivierung und hoch regioselektiver Alkininsertion erzeugt ein breites Spektrum an Spirooxindolen und Spirodihydrobenzofuranen. Die Spirocyclen werden in guten bis hervorragenden Ausbeuten und mit Regioisomerenverhältnissen >20:1 erhalten.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201706325</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Activation ; Alkine ; Alkynes ; C-H-Aktivierung ; Chemistry ; Insertion ; Palladium ; Regioselectivity ; Regioselektivität ; Spiroverbindungen</subject><ispartof>Angewandte Chemie, 2017-08, Vol.129 (36), p.11060-11063</ispartof><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-c1625-21ef1f8a1915fb1b567a17cf1232291872ea9b6c8a469fbc1f510f183d222a0f3</citedby><cites>FETCH-LOGICAL-c1625-21ef1f8a1915fb1b567a17cf1232291872ea9b6c8a469fbc1f510f183d222a0f3</cites><orcidid>0000-0001-9867-9178</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%2Fange.201706325$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201706325$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Yoon, Hyung</creatorcontrib><creatorcontrib>Rölz, Martin</creatorcontrib><creatorcontrib>Landau, Felicitas</creatorcontrib><creatorcontrib>Lautens, Mark</creatorcontrib><title>Palladium‐Catalyzed Spirocyclization through C−H Activation and Regioselective Alkyne Insertion</title><title>Angewandte Chemie</title><description>A Pd‐catalyzed spirocyclization involving a sequential carbopalladation, intramolecular C−H activation, and a highly regioselective alkyne insertion to afford spirooxindoles and spirodihydrobenzofurans has been achieved. The spirocyclic products were generated in good to excellent yields with complete regiocontrol in a readily scalable procedure.
Punktgenau verknüpft: Eine Pd‐katalysierte Reaktionskaskade aus sequenzieller Carbopalladierung, intramolekularer C‐H‐Aktivierung und hoch regioselektiver Alkininsertion erzeugt ein breites Spektrum an Spirooxindolen und Spirodihydrobenzofuranen. Die Spirocyclen werden in guten bis hervorragenden Ausbeuten und mit Regioisomerenverhältnissen >20:1 erhalten.</description><subject>Activation</subject><subject>Alkine</subject><subject>Alkynes</subject><subject>C-H-Aktivierung</subject><subject>Chemistry</subject><subject>Insertion</subject><subject>Palladium</subject><subject>Regioselectivity</subject><subject>Regioselektivität</subject><subject>Spiroverbindungen</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwMkdiTvE5nx6jqNBKFSA-Zstx7NbFTYqdgtKJkRHxE_tLaBQEI9NJ7z3vnfQgdA54BBiTS17N5YhgSHAckOgADSAi4AdJlByiAcZh6KckpMfoxLklxjgmCR0gcceN4aXerHbvnzlvuGm3svQe1trWohVGb3mj68prFrbezBdevvv4mniZaPRrv-BV6d3Lua6dNLKLpZeZ57aS3rRy0nbMKTpS3Dh59jOH6Olq_JhP_Nnt9TTPZr6AmEQ-AalApRwoRKqAIooTDolQQAJCKKQJkZwWsUh5GFNVCFARYAVpUBJCOFbBEF30d9e2ftlI17BlvbHV_iUDGgChYQrBnhr1lLC1c1YqtrZ6xW3LALNOJOtEsl-R-wLtC2_ayPYfmmU31-O_7jfDsHor</recordid><startdate>20170828</startdate><enddate>20170828</enddate><creator>Yoon, Hyung</creator><creator>Rölz, Martin</creator><creator>Landau, Felicitas</creator><creator>Lautens, Mark</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-9867-9178</orcidid></search><sort><creationdate>20170828</creationdate><title>Palladium‐Catalyzed Spirocyclization through C−H Activation and Regioselective Alkyne Insertion</title><author>Yoon, Hyung ; Rölz, Martin ; Landau, Felicitas ; Lautens, Mark</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1625-21ef1f8a1915fb1b567a17cf1232291872ea9b6c8a469fbc1f510f183d222a0f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Activation</topic><topic>Alkine</topic><topic>Alkynes</topic><topic>C-H-Aktivierung</topic><topic>Chemistry</topic><topic>Insertion</topic><topic>Palladium</topic><topic>Regioselectivity</topic><topic>Regioselektivität</topic><topic>Spiroverbindungen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoon, Hyung</creatorcontrib><creatorcontrib>Rölz, Martin</creatorcontrib><creatorcontrib>Landau, Felicitas</creatorcontrib><creatorcontrib>Lautens, Mark</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yoon, Hyung</au><au>Rölz, Martin</au><au>Landau, Felicitas</au><au>Lautens, Mark</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium‐Catalyzed Spirocyclization through C−H Activation and Regioselective Alkyne Insertion</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-08-28</date><risdate>2017</risdate><volume>129</volume><issue>36</issue><spage>11060</spage><epage>11063</epage><pages>11060-11063</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A Pd‐catalyzed spirocyclization involving a sequential carbopalladation, intramolecular C−H activation, and a highly regioselective alkyne insertion to afford spirooxindoles and spirodihydrobenzofurans has been achieved. The spirocyclic products were generated in good to excellent yields with complete regiocontrol in a readily scalable procedure.
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Activation Alkine Alkynes C-H-Aktivierung Chemistry Insertion Palladium Regioselectivity Regioselektivität Spiroverbindungen |
| title | Palladium‐Catalyzed Spirocyclization through C−H Activation and Regioselective Alkyne Insertion |
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