Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light
A metal‐ and oxidant‐free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selec...
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| Veröffentlicht in: | Chemistry : a European journal 2019-06, Vol.25 (35), p.8225-8228 |
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| container_issue | 35 |
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| container_title | Chemistry : a European journal |
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| creator | Zhang, Yueteng Ji, Peng Hu, Wenbo Wei, Yongyi Huang, He Wang, Wei |
| description | A metal‐ and oxidant‐free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late‐stage modification of complex structures, which are difficult to achieve with the existing protocols.
Without metals and oxidants! A 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer with visible light was successfully implemented to selectively generate acyl radicals from aldehydes and produce a metal‐ and oxidant‐free method for accessing structurally diverse thioesters. |
| doi_str_mv | 10.1002/chem.201900932 |
| format | Article |
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Without metals and oxidants! A 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer with visible light was successfully implemented to selectively generate acyl radicals from aldehydes and produce a metal‐ and oxidant‐free method for accessing structurally diverse thioesters.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201900932</identifier><identifier>PMID: 30986322</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Catalysis ; Chemistry ; Crossovers ; Functional groups ; organocatalysis ; photochemistry ; Substrates ; Thioesters</subject><ispartof>Chemistry : a European journal, 2019-06, Vol.25 (35), p.8225-8228</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4102-f11eba9a5fc095685e1f9b02816fdb8c4102a790180a9fdd3e32929128544d003</citedby><cites>FETCH-LOGICAL-c4102-f11eba9a5fc095685e1f9b02816fdb8c4102a790180a9fdd3e32929128544d003</cites><orcidid>0000-0001-6043-0860</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%2Fchem.201900932$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201900932$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30986322$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Yueteng</creatorcontrib><creatorcontrib>Ji, Peng</creatorcontrib><creatorcontrib>Hu, Wenbo</creatorcontrib><creatorcontrib>Wei, Yongyi</creatorcontrib><creatorcontrib>Huang, He</creatorcontrib><creatorcontrib>Wang, Wei</creatorcontrib><title>Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A metal‐ and oxidant‐free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late‐stage modification of complex structures, which are difficult to achieve with the existing protocols.
Without metals and oxidants! A 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer with visible light was successfully implemented to selectively generate acyl radicals from aldehydes and produce a metal‐ and oxidant‐free method for accessing structurally diverse thioesters.</description><subject>Aldehydes</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Crossovers</subject><subject>Functional groups</subject><subject>organocatalysis</subject><subject>photochemistry</subject><subject>Substrates</subject><subject>Thioesters</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQQC0EoqWwMqJIzClnO3bisaqAIgV1KayRk9iNqyQudqoqf09KSxmZbnn37vQQuscwxQDkqahUMyWABYCg5AKNMSM4pDFnl2gMIopDzqgYoRvvNzAwnNJrNKIgEk4JGaN06daytYXsZN13pghWTrZeW9fIztg2sDqY1aWq-lL5oLPBqjJW-U45H-xNVwWfxpu8VkFq1lV3i660rL26O80J-nh5Xs0XYbp8fZvP0rCIMJBQY6xyKSTTBQjGE6awFjmQBHNd5skPJGMBOAEpdFlSRYkgApOERVEJQCfo8ejdOvu1G97JNnbn2uFkRgijPOZ8qDFB0yNVOOu9UzrbOtNI12cYskO87BAvO8cbFh5O2l3eqPKM_9YaAHEE9qZW_T-6bL54fv-TfwOlAnq6</recordid><startdate>20190621</startdate><enddate>20190621</enddate><creator>Zhang, Yueteng</creator><creator>Ji, Peng</creator><creator>Hu, Wenbo</creator><creator>Wei, Yongyi</creator><creator>Huang, He</creator><creator>Wang, Wei</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><orcidid>https://orcid.org/0000-0001-6043-0860</orcidid></search><sort><creationdate>20190621</creationdate><title>Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light</title><author>Zhang, Yueteng ; Ji, Peng ; Hu, Wenbo ; Wei, Yongyi ; Huang, He ; Wang, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4102-f11eba9a5fc095685e1f9b02816fdb8c4102a790180a9fdd3e32929128544d003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aldehydes</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Crossovers</topic><topic>Functional groups</topic><topic>organocatalysis</topic><topic>photochemistry</topic><topic>Substrates</topic><topic>Thioesters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Yueteng</creatorcontrib><creatorcontrib>Ji, Peng</creatorcontrib><creatorcontrib>Hu, Wenbo</creatorcontrib><creatorcontrib>Wei, Yongyi</creatorcontrib><creatorcontrib>Huang, He</creatorcontrib><creatorcontrib>Wang, Wei</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Yueteng</au><au>Ji, Peng</au><au>Hu, Wenbo</au><au>Wei, Yongyi</au><au>Huang, He</au><au>Wang, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-06-21</date><risdate>2019</risdate><volume>25</volume><issue>35</issue><spage>8225</spage><epage>8228</epage><pages>8225-8228</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A metal‐ and oxidant‐free catalytic method for accessing structurally diverse thioesters from readily accessible, widespread aldehydes, is described. A strategy of a simple organic 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer (HAT) with visible light was successfully implemented to selectively generate acyl radicals without inducing crossover reactivity of thioester products. The preparative power of the method was demonstrated by broad substrate scope and wide functional group tolerance, and enabled the late‐stage modification of complex structures, which are difficult to achieve with the existing protocols.
Without metals and oxidants! A 9,10‐phenanthrenequinone‐promoted hydrogen atom transfer with visible light was successfully implemented to selectively generate acyl radicals from aldehydes and produce a metal‐ and oxidant‐free method for accessing structurally diverse thioesters.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30986322</pmid><doi>10.1002/chem.201900932</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-6043-0860</orcidid></addata></record> |
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| language | eng |
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| source | Access via Wiley Online Library |
| subjects | Aldehydes Catalysis Chemistry Crossovers Functional groups organocatalysis photochemistry Substrates Thioesters |
| title | Organocatalytic Transformation of Aldehydes to Thioesters with Visible Light |
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