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 International Edition 2015-09, Vol.54 (36), p.10648-10651 |
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| container_title | Angewandte Chemie International Edition |
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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.
A cascade process that is triggered by an intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene leads to the formation of 4‐substituted cycloocta‐2,5‐dien‐1‐ones. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields. |
| doi_str_mv | 10.1002/anie.201505347 |
| format | Article |
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A cascade process that is triggered by an intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene leads to the formation of 4‐substituted cycloocta‐2,5‐dien‐1‐ones. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201505347</identifier><identifier>PMID: 26230528</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehydes ; Allene ; annulation ; Aromatic compounds ; carbocycles ; Cascades ; Chlorides ; Communications ; Derivatives ; Formations ; Hydrides ; medium-ring compounds ; Synthesis ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2015-09, Vol.54 (36), p.10648-10651</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><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. 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6747-6edd2148c92d39091c0afa509ae68006b6f0b346b8dc5ab08b2cf09c6975495f3</citedby><cites>FETCH-LOGICAL-c6747-6edd2148c92d39091c0afa509ae68006b6f0b346b8dc5ab08b2cf09c6975495f3</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.201505347$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201505347$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26230528$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></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 International Edition</title><addtitle>Angew. Chem. Int. Ed</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.
A cascade process that is triggered by an intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene leads to the formation of 4‐substituted cycloocta‐2,5‐dien‐1‐ones. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.</description><subject>Aldehydes</subject><subject>Allene</subject><subject>annulation</subject><subject>Aromatic compounds</subject><subject>carbocycles</subject><subject>Cascades</subject><subject>Chlorides</subject><subject>Communications</subject><subject>Derivatives</subject><subject>Formations</subject><subject>Hydrides</subject><subject>medium-ring compounds</subject><subject>Synthesis</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqNks1rFEEQxQdRTIxePcqAlwj22t8fl8C6ZJNASMQoHpuenhp34mz32j2rbv56O2xcogf1VAX1e4-q4lXVc4InBGP6xoUeJhQTgQXj6kG1TwQliCnFHpaeM4aUFmSvepLzdeG1xvJxtUclZVhQvV-tLgOgd3GsZy6E_ubGpVja7F0L9dUmjAvIfa5jV8c0LiKarzO09Wzjhxj96BB9LVDbQ0AExQC57lJc1hS9LSUeLmCEFF-5tBnq6dDCYtNCflo96tyQ4dldPag-zo8_zE7R-eXJ2Wx6jrxUXCEJbUsJ197QlhlsiMeucwIbB1JjLBvZ4YZx2ejWC9dg3VDfYeOlUYIb0bGD6mjru1o3S2g9hDG5wa5SvywL2eh6-_sk9Av7OX6zXGjCpSgGh3cGKX5dQx7tss8ehsEFiOtsieJcGq6p_A-UMEEVN6qgL_9Ar-M6hfIJSww1WEgi9V8phaUgRClTqMmW8inmnKDbXUewvU2HvU2H3aWjCF7c_8kO_xWHApgt8L0fYPMPOzu9ODu-b4622j6P8GOndemLlYopYT9dnNirOSfvycWpnbGfLkPUBg</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>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>5PM</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-c6747-6edd2148c92d39091c0afa509ae68006b6f0b346b8dc5ab08b2cf09c6975495f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Aldehydes</topic><topic>Allene</topic><topic>annulation</topic><topic>Aromatic compounds</topic><topic>carbocycles</topic><topic>Cascades</topic><topic>Chlorides</topic><topic>Communications</topic><topic>Derivatives</topic><topic>Formations</topic><topic>Hydrides</topic><topic>medium-ring compounds</topic><topic>Synthesis</topic><topic>synthetic methods</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>Wiley Online Library (Open Access Collection)</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Angewandte Chemie International Edition</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 International Edition</jtitle><addtitle>Angew. 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A cascade process that is triggered by an intramolecular Cannizzaro‐type hydride transfer to an in situ prepared allene leads to the formation of 4‐substituted cycloocta‐2,5‐dien‐1‐ones. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26230528</pmid><doi>10.1002/anie.201505347</doi><tpages>4</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | Aldehydes Allene annulation Aromatic compounds carbocycles Cascades Chlorides Communications Derivatives Formations Hydrides medium-ring compounds Synthesis synthetic methods |
| 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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