[2+2] Cycloaddition of 1,3-Dienes by Visible Light Photocatalysis
[2+2] Photocycloadditions of 1,3‐dienes represent a powerful yet synthetically underutilized class of reactions. We report that visible light absorbing transition metal complexes enable the [2+2] cycloaddition of a diverse range of 1,3‐dienes. The ability to use long‐wavelength visible light is attr...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-08, Vol.53 (34), p.8991-8994 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Hurtley, Anna E. Lu, Zhan Yoon, Tehshik P. |
| description | [2+2] Photocycloadditions of 1,3‐dienes represent a powerful yet synthetically underutilized class of reactions. We report that visible light absorbing transition metal complexes enable the [2+2] cycloaddition of a diverse range of 1,3‐dienes. The ability to use long‐wavelength visible light is attractive because these reaction conditions tolerate the presence of sensitive functional groups that might be readily decomposed by the high‐energy UVC radiation required for direct photoexcitation of 1,3‐dienes. The resulting vinylcyclobutane products are poised for a variety of further diversification reactions, and this method is consequently expected to be powerfully enabling in the synthesis of complex organic targets.
Square dance: A convenient and highly functional‐group‐tolerant [2+2] cycloaddition of 1,3‐dienes that operates under visible light irradiation is reported. The vinylcyclobutane products serve as versatile synthetic intermediates in a range of further transformations as illustrated by a concise synthesis of the marine natural product (±)‐epiraikovenal. bpy=bipyridyl, ppy=phenylpyridyl. |
| doi_str_mv | 10.1002/anie.201405359 |
| format | Article |
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Square dance: A convenient and highly functional‐group‐tolerant [2+2] cycloaddition of 1,3‐dienes that operates under visible light irradiation is reported. The vinylcyclobutane products serve as versatile synthetic intermediates in a range of further transformations as illustrated by a concise synthesis of the marine natural product (±)‐epiraikovenal. bpy=bipyridyl, ppy=phenylpyridyl.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201405359</identifier><identifier>PMID: 24985967</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Absorption ; Catalysis ; Cycloaddition ; Cycloaddition Reaction ; cycloadditions ; energy transfer ; Functional groups ; Light ; Light irradiation ; Marine ; Photochemical Processes ; photochemistry ; Photoexcitation ; small ring systems ; Synthesis ; total synthesis ; Transformations ; Transition metals</subject><ispartof>Angewandte Chemie International Edition, 2014-08, Vol.53 (34), p.8991-8994</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6429-5dbc28cdb544865c11bf1e3d0c9ed88a070a36f383017294da0a79d59fd211303</citedby><cites>FETCH-LOGICAL-c6429-5dbc28cdb544865c11bf1e3d0c9ed88a070a36f383017294da0a79d59fd211303</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.201405359$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201405359$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24985967$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hurtley, Anna E.</creatorcontrib><creatorcontrib>Lu, Zhan</creatorcontrib><creatorcontrib>Yoon, Tehshik P.</creatorcontrib><title>[2+2] Cycloaddition of 1,3-Dienes by Visible Light Photocatalysis</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>[2+2] Photocycloadditions of 1,3‐dienes represent a powerful yet synthetically underutilized class of reactions. We report that visible light absorbing transition metal complexes enable the [2+2] cycloaddition of a diverse range of 1,3‐dienes. The ability to use long‐wavelength visible light is attractive because these reaction conditions tolerate the presence of sensitive functional groups that might be readily decomposed by the high‐energy UVC radiation required for direct photoexcitation of 1,3‐dienes. The resulting vinylcyclobutane products are poised for a variety of further diversification reactions, and this method is consequently expected to be powerfully enabling in the synthesis of complex organic targets.
Square dance: A convenient and highly functional‐group‐tolerant [2+2] cycloaddition of 1,3‐dienes that operates under visible light irradiation is reported. The vinylcyclobutane products serve as versatile synthetic intermediates in a range of further transformations as illustrated by a concise synthesis of the marine natural product (±)‐epiraikovenal. bpy=bipyridyl, ppy=phenylpyridyl.</description><subject>Absorption</subject><subject>Catalysis</subject><subject>Cycloaddition</subject><subject>Cycloaddition Reaction</subject><subject>cycloadditions</subject><subject>energy transfer</subject><subject>Functional groups</subject><subject>Light</subject><subject>Light irradiation</subject><subject>Marine</subject><subject>Photochemical Processes</subject><subject>photochemistry</subject><subject>Photoexcitation</subject><subject>small ring systems</subject><subject>Synthesis</subject><subject>total synthesis</subject><subject>Transformations</subject><subject>Transition metals</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkV2L1DAUhoso7ofeeikFbwTteE4-muRGGGfXcWFYFfwARUKapDtZO83adNT-e1tmHVZv9ioH8rwPJ3mz7BHCDAHIC9MGPyOADDjl6k52iJxgQYWgd8eZUVoIyfEgO0rpcuSlhPJ-dkCYklyV4jCbfyXPyLd8MdgmGudCH2KbxzrH57Q4Cb71Ka-G_FNIoWp8vgoX6z5_t459tKY3zZBCepDdq02T_MPr8zj7-Pr0w-JNsXq7PFvMV4UtGVEFd5Ul0rqKMyZLbhGrGj11YJV3UhoQYGhZU0kBBVHMGTBCOa5qRxAp0OPs5c57ta023lnf9p1p9FUXNqYbdDRB_3vThrW-iD81Q8oEmwRPrwVd_LH1qdebkKxvGtP6uE0aBSAoUILfjnJOBZQKJvTJf-hl3Hbt-BMTRSTKkrCRmu0o28WUOl_v90bQU5F6KlLvixwDj2--do__bW4E1A74FRo_3KLT8_Oz05vyYpcNqfe_91nTfdejWXD9-Xypx9befyGvlprTP6ZFtqk</recordid><startdate>20140818</startdate><enddate>20140818</enddate><creator>Hurtley, Anna E.</creator><creator>Lu, Zhan</creator><creator>Yoon, Tehshik P.</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><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>5PM</scope></search><sort><creationdate>20140818</creationdate><title>[2+2] Cycloaddition of 1,3-Dienes by Visible Light Photocatalysis</title><author>Hurtley, Anna E. ; Lu, Zhan ; Yoon, Tehshik P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6429-5dbc28cdb544865c11bf1e3d0c9ed88a070a36f383017294da0a79d59fd211303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Absorption</topic><topic>Catalysis</topic><topic>Cycloaddition</topic><topic>Cycloaddition Reaction</topic><topic>cycloadditions</topic><topic>energy transfer</topic><topic>Functional groups</topic><topic>Light</topic><topic>Light irradiation</topic><topic>Marine</topic><topic>Photochemical Processes</topic><topic>photochemistry</topic><topic>Photoexcitation</topic><topic>small ring systems</topic><topic>Synthesis</topic><topic>total synthesis</topic><topic>Transformations</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hurtley, Anna E.</creatorcontrib><creatorcontrib>Lu, Zhan</creatorcontrib><creatorcontrib>Yoon, Tehshik P.</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><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>Hurtley, Anna E.</au><au>Lu, Zhan</au><au>Yoon, Tehshik P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>[2+2] Cycloaddition of 1,3-Dienes by Visible Light Photocatalysis</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-08-18</date><risdate>2014</risdate><volume>53</volume><issue>34</issue><spage>8991</spage><epage>8994</epage><pages>8991-8994</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>[2+2] Photocycloadditions of 1,3‐dienes represent a powerful yet synthetically underutilized class of reactions. We report that visible light absorbing transition metal complexes enable the [2+2] cycloaddition of a diverse range of 1,3‐dienes. The ability to use long‐wavelength visible light is attractive because these reaction conditions tolerate the presence of sensitive functional groups that might be readily decomposed by the high‐energy UVC radiation required for direct photoexcitation of 1,3‐dienes. The resulting vinylcyclobutane products are poised for a variety of further diversification reactions, and this method is consequently expected to be powerfully enabling in the synthesis of complex organic targets.
Square dance: A convenient and highly functional‐group‐tolerant [2+2] cycloaddition of 1,3‐dienes that operates under visible light irradiation is reported. The vinylcyclobutane products serve as versatile synthetic intermediates in a range of further transformations as illustrated by a concise synthesis of the marine natural product (±)‐epiraikovenal. bpy=bipyridyl, ppy=phenylpyridyl.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24985967</pmid><doi>10.1002/anie.201405359</doi><tpages>4</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Absorption Catalysis Cycloaddition Cycloaddition Reaction cycloadditions energy transfer Functional groups Light Light irradiation Marine Photochemical Processes photochemistry Photoexcitation small ring systems Synthesis total synthesis Transformations Transition metals |
| title | [2+2] Cycloaddition of 1,3-Dienes by Visible Light Photocatalysis |
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