One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
An intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene enables the synthesis of ortho‐fused 4‐substituted cycloocta‐2,5‐dien‐1‐ones with unprecedented technical ease for an eight‐ring carboannulation. Various derivatives could be obtained from commercially available (hetero...
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| Veröffentlicht in: | Angewandte Chemie 2015-09, Vol.127 (36), p.10794-10797 |
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| container_issue | 36 |
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| container_title | Angewandte Chemie |
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| creator | Burroughs, Laurence Eccleshare, Lee Ritchie, John Kulkarni, Omkar Lygo, Barry Woodward, Simon Lewis, William |
| description | An intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene enables the synthesis of ortho‐fused 4‐substituted cycloocta‐2,5‐dien‐1‐ones with unprecedented technical ease for an eight‐ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.
Eine Reaktionskaskade, die von einer intramolekularen Cannizzaro‐artigen Hydridwanderung zu einem in situ hergestellten Allen ausgelöst wird, führt zu 4‐substituierten Cycloocta‐2,5‐dien‐1‐onen. Verschiedene Derivate konnten ausgehend von kommerziell erhältlichen (Hetero)arylaldehyden, Trimethylsilylacetylen und einfachen Propargylchloriden in guten Ausbeuten erhalten werden. |
| doi_str_mv | 10.1002/ange.201505347 |
| format | Article |
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Eine Reaktionskaskade, die von einer intramolekularen Cannizzaro‐artigen Hydridwanderung zu einem in situ hergestellten Allen ausgelöst wird, führt zu 4‐substituierten Cycloocta‐2,5‐dien‐1‐onen. Verschiedene Derivate konnten ausgehend von kommerziell erhältlichen (Hetero)arylaldehyden, Trimethylsilylacetylen und einfachen Propargylchloriden in guten Ausbeuten erhalten werden.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201505347</identifier><language>eng ; ger</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehyde ; Aldehydes ; Allene ; Anellierung ; Aromatic compounds ; Carbocyclen ; Cascades ; Chemistry ; Chlorides ; Derivatives ; Hydrides ; Mittlere Ringe ; Synthesemethoden ; Synthesis</subject><ispartof>Angewandte Chemie, 2015-09, Vol.127 (36), p.10794-10797</ispartof><rights>2015 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</rights><rights>2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3017-af3c1cc1bedaa93f873c894668af2b39970dc330224378735d15435fad1350433</citedby><cites>FETCH-LOGICAL-c3017-af3c1cc1bedaa93f873c894668af2b39970dc330224378735d15435fad1350433</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%2Fange.201505347$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201505347$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Burroughs, Laurence</creatorcontrib><creatorcontrib>Eccleshare, Lee</creatorcontrib><creatorcontrib>Ritchie, John</creatorcontrib><creatorcontrib>Kulkarni, Omkar</creatorcontrib><creatorcontrib>Lygo, Barry</creatorcontrib><creatorcontrib>Woodward, Simon</creatorcontrib><creatorcontrib>Lewis, William</creatorcontrib><title>One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>An intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene enables the synthesis of ortho‐fused 4‐substituted cycloocta‐2,5‐dien‐1‐ones with unprecedented technical ease for an eight‐ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.
Eine Reaktionskaskade, die von einer intramolekularen Cannizzaro‐artigen Hydridwanderung zu einem in situ hergestellten Allen ausgelöst wird, führt zu 4‐substituierten Cycloocta‐2,5‐dien‐1‐onen. Verschiedene Derivate konnten ausgehend von kommerziell erhältlichen (Hetero)arylaldehyden, Trimethylsilylacetylen und einfachen Propargylchloriden in guten Ausbeuten erhalten werden.</description><subject>Aldehyde</subject><subject>Aldehydes</subject><subject>Allene</subject><subject>Anellierung</subject><subject>Aromatic compounds</subject><subject>Carbocyclen</subject><subject>Cascades</subject><subject>Chemistry</subject><subject>Chlorides</subject><subject>Derivatives</subject><subject>Hydrides</subject><subject>Mittlere Ringe</subject><subject>Synthesemethoden</subject><subject>Synthesis</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkU1vEzEQhleISoTClfNKXIqEw_hrvT6GqE0RVYoECG6Wa8-SLRs72BvB9tfjKqhCPbSnGcnPMx7NW1WvKMwpAHtnww-cM6ASJBfqSTWjklHClVRPqxmAEKRlQj-rnud8DQANU3pW7S4Dkk9xrJc2hP7mxqZY2uysx_rzFMYN5j7XsatjGjeRnO0z-no5uSFGN1rC3kriewyEkhgw112K25qR96XEkw2OmOIbm6ahXgweN5PH_KI66uyQ8eW_elx9PTv9sjwnF5erD8vFBXEcqCK24446R6_QW6t51yruWi2aprUdu-JaK_COc2BMcFUepadScNlZT7kEwflxdXKYu0vx1x7zaLZ9djgMNmDcZ0OVEAqAUlHQ1_fQ67hPoWxnqGYapGiBPUgpaCQ05f9CzQ-USzHnhJ3ZpX5bTmAomNuYzG1M5i6mIuiD8LsfcHqENov16vR_lxzcPo_458616adpVAnefFuvzPe14MA_nhvJ_wKKraKK</recordid><startdate>20150901</startdate><enddate>20150901</enddate><creator>Burroughs, Laurence</creator><creator>Eccleshare, Lee</creator><creator>Ritchie, John</creator><creator>Kulkarni, Omkar</creator><creator>Lygo, Barry</creator><creator>Woodward, Simon</creator><creator>Lewis, William</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>24P</scope><scope>WIN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150901</creationdate><title>One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes</title><author>Burroughs, Laurence ; Eccleshare, Lee ; Ritchie, John ; Kulkarni, Omkar ; Lygo, Barry ; Woodward, Simon ; Lewis, William</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3017-af3c1cc1bedaa93f873c894668af2b39970dc330224378735d15435fad1350433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng ; ger</language><creationdate>2015</creationdate><topic>Aldehyde</topic><topic>Aldehydes</topic><topic>Allene</topic><topic>Anellierung</topic><topic>Aromatic compounds</topic><topic>Carbocyclen</topic><topic>Cascades</topic><topic>Chemistry</topic><topic>Chlorides</topic><topic>Derivatives</topic><topic>Hydrides</topic><topic>Mittlere Ringe</topic><topic>Synthesemethoden</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Burroughs, Laurence</creatorcontrib><creatorcontrib>Eccleshare, Lee</creatorcontrib><creatorcontrib>Ritchie, John</creatorcontrib><creatorcontrib>Kulkarni, Omkar</creatorcontrib><creatorcontrib>Lygo, Barry</creatorcontrib><creatorcontrib>Woodward, Simon</creatorcontrib><creatorcontrib>Lewis, William</creatorcontrib><collection>Istex</collection><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library Free Content</collection><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>Burroughs, Laurence</au><au>Eccleshare, Lee</au><au>Ritchie, John</au><au>Kulkarni, Omkar</au><au>Lygo, Barry</au><au>Woodward, Simon</au><au>Lewis, William</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-09-01</date><risdate>2015</risdate><volume>127</volume><issue>36</issue><spage>10794</spage><epage>10797</epage><pages>10794-10797</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>An intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene enables the synthesis of ortho‐fused 4‐substituted cycloocta‐2,5‐dien‐1‐ones with unprecedented technical ease for an eight‐ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.
Eine Reaktionskaskade, die von einer intramolekularen Cannizzaro‐artigen Hydridwanderung zu einem in situ hergestellten Allen ausgelöst wird, führt zu 4‐substituierten Cycloocta‐2,5‐dien‐1‐onen. Verschiedene Derivate konnten ausgehend von kommerziell erhältlichen (Hetero)arylaldehyden, Trimethylsilylacetylen und einfachen Propargylchloriden in guten Ausbeuten erhalten werden.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201505347</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehyde Aldehydes Allene Anellierung Aromatic compounds Carbocyclen Cascades Chemistry Chlorides Derivatives Hydrides Mittlere Ringe Synthesemethoden Synthesis |
| title | One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes |
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