A One‐Pot Approach for Bio‐Based Arylamines via a Combined Photooxidative Dearomatization‐Rearomatization Strategy
The synthesis of arylamines from renewable resources under mild reaction conditions is highly desired for the sustainability of the chemical industry, where the production of hazardous waste is a prime concern. However, to date, there are very few tools in chemists’ toolboxes that are able to produc...
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Veröffentlicht in: | Chemistry : a European journal 2022-06, Vol.28 (34), p.e202200309-n/a |
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creator | Afanasenko, Anastasiia Kavun, Aleksei Thomas, Dylan Li, Chao‐Jun |
description | The synthesis of arylamines from renewable resources under mild reaction conditions is highly desired for the sustainability of the chemical industry, where the production of hazardous waste is a prime concern. However, to date, there are very few tools in chemists’ toolboxes that are able to produce arylamines in a sustainable manner. Herein, a robust one‐pot approach for constructing bio‐based arylamines via a combined photooxidative dearomatization‐rearomatization strategy is presented. The developed methodology enables the synthesis of structurally complex amines in moderate‐to‐good isolated yields using biomass‐derived phenols, natural α‐amino acids, and naphthols under remarkably mild reaction conditions. For the photooxygenation of phenols, a novel chrysazine‐based catalyst system was introduced, demonstrating its efficiency for the synthesis of natural products – hallerone, rengyolone, and the pharmaceutically relevant prodrug DHED.
Two‐for‐one: Arylamines were obtained from biomass‐derived phenolic substrates and cyclic α‐amino acids by combining photooxidative dearomatization with decarboxylation/azomethine ylide chemistry. A novel organophotocatalytic approach was reported for the synthesis of a wide range of p‐quinols, including natural products and pharmaceutically‐relevant compounds. |
doi_str_mv | 10.1002/chem.202200309 |
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Two‐for‐one: Arylamines were obtained from biomass‐derived phenolic substrates and cyclic α‐amino acids by combining photooxidative dearomatization with decarboxylation/azomethine ylide chemistry. A novel organophotocatalytic approach was reported for the synthesis of a wide range of p‐quinols, including natural products and pharmaceutically‐relevant compounds.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202200309</identifier><identifier>PMID: 35393648</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Amines ; Amino acids ; arylamines ; Catalysts ; Chemical industry ; Chemistry ; Chemists ; dearomatization-rearomatization ; Hazardous wastes ; Natural products ; Organic compounds ; phenol-amine coupling ; Phenols ; photooxidation ; Renewable resources ; singlet oxygen ; Sustainability ; Sustainable yield</subject><ispartof>Chemistry : a European journal, 2022-06, Vol.28 (34), p.e202200309-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3739-993646a47a427ad4886dfc1bf5da7f7cea37b0b4fee801ff3b055a669db29e823</citedby><cites>FETCH-LOGICAL-c3739-993646a47a427ad4886dfc1bf5da7f7cea37b0b4fee801ff3b055a669db29e823</cites><orcidid>0000-0001-7234-8290 ; 0000-0002-4541-6339 ; 0000-0002-3859-8824</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.202200309$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202200309$$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/35393648$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Afanasenko, Anastasiia</creatorcontrib><creatorcontrib>Kavun, Aleksei</creatorcontrib><creatorcontrib>Thomas, Dylan</creatorcontrib><creatorcontrib>Li, Chao‐Jun</creatorcontrib><title>A One‐Pot Approach for Bio‐Based Arylamines via a Combined Photooxidative Dearomatization‐Rearomatization Strategy</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>The synthesis of arylamines from renewable resources under mild reaction conditions is highly desired for the sustainability of the chemical industry, where the production of hazardous waste is a prime concern. However, to date, there are very few tools in chemists’ toolboxes that are able to produce arylamines in a sustainable manner. Herein, a robust one‐pot approach for constructing bio‐based arylamines via a combined photooxidative dearomatization‐rearomatization strategy is presented. The developed methodology enables the synthesis of structurally complex amines in moderate‐to‐good isolated yields using biomass‐derived phenols, natural α‐amino acids, and naphthols under remarkably mild reaction conditions. For the photooxygenation of phenols, a novel chrysazine‐based catalyst system was introduced, demonstrating its efficiency for the synthesis of natural products – hallerone, rengyolone, and the pharmaceutically relevant prodrug DHED.
Two‐for‐one: Arylamines were obtained from biomass‐derived phenolic substrates and cyclic α‐amino acids by combining photooxidative dearomatization with decarboxylation/azomethine ylide chemistry. A novel organophotocatalytic approach was reported for the synthesis of a wide range of p‐quinols, including natural products and pharmaceutically‐relevant compounds.</description><subject>Amines</subject><subject>Amino acids</subject><subject>arylamines</subject><subject>Catalysts</subject><subject>Chemical industry</subject><subject>Chemistry</subject><subject>Chemists</subject><subject>dearomatization-rearomatization</subject><subject>Hazardous wastes</subject><subject>Natural products</subject><subject>Organic compounds</subject><subject>phenol-amine coupling</subject><subject>Phenols</subject><subject>photooxidation</subject><subject>Renewable resources</subject><subject>singlet oxygen</subject><subject>Sustainability</subject><subject>Sustainable yield</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkc1u1DAUha0K1A6l2y6RJTZsMvgnsePldGgpUqtWQNfWTXLNpEriwc60HVY8As_Ik-DR9Ed004Vl36PPR_feQ8ghZ1POmPhYL7CfCiYEY5KZHTLhheCZ1Kp4RSbM5DpThTR75E2M14wxo6TcJXsyaVLl5YTczejFgH9__7n0I50tl8FDvaDOB3rU-iQfQcSGzsK6g74dMNKbFijQue-rVDb0cuFH7-_aBsb2BuknhOD79P6Vjh-Swdf_FfptDDDij_Vb8tpBF_Hg_t4nVyfH3-en2dnF5y_z2VlWSy1NZjZ9Ksg15EJDk5elalzNK1c0oJ2uEaSuWJU7xJJx52TFigKUMk0lDJZC7pMPW9802s8VxtH2bayx62BAv4pWpDWURiudJ_T9M_Tar8KQurNCC660KblK1HRL1cHHGNDZZWh7CGvLmd1kYjeZ2MdM0od397arqsfmEX8IIQFmC9y2Ha5fsLPz0-PzJ_N_i-ecnQ</recordid><startdate>20220615</startdate><enddate>20220615</enddate><creator>Afanasenko, Anastasiia</creator><creator>Kavun, Aleksei</creator><creator>Thomas, Dylan</creator><creator>Li, Chao‐Jun</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><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7234-8290</orcidid><orcidid>https://orcid.org/0000-0002-4541-6339</orcidid><orcidid>https://orcid.org/0000-0002-3859-8824</orcidid></search><sort><creationdate>20220615</creationdate><title>A One‐Pot Approach for Bio‐Based Arylamines via a Combined Photooxidative Dearomatization‐Rearomatization Strategy</title><author>Afanasenko, Anastasiia ; Kavun, Aleksei ; Thomas, Dylan ; Li, Chao‐Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3739-993646a47a427ad4886dfc1bf5da7f7cea37b0b4fee801ff3b055a669db29e823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Amines</topic><topic>Amino acids</topic><topic>arylamines</topic><topic>Catalysts</topic><topic>Chemical industry</topic><topic>Chemistry</topic><topic>Chemists</topic><topic>dearomatization-rearomatization</topic><topic>Hazardous wastes</topic><topic>Natural products</topic><topic>Organic compounds</topic><topic>phenol-amine coupling</topic><topic>Phenols</topic><topic>photooxidation</topic><topic>Renewable resources</topic><topic>singlet oxygen</topic><topic>Sustainability</topic><topic>Sustainable yield</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Afanasenko, Anastasiia</creatorcontrib><creatorcontrib>Kavun, Aleksei</creatorcontrib><creatorcontrib>Thomas, Dylan</creatorcontrib><creatorcontrib>Li, Chao‐Jun</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><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Afanasenko, Anastasiia</au><au>Kavun, Aleksei</au><au>Thomas, Dylan</au><au>Li, Chao‐Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A One‐Pot Approach for Bio‐Based Arylamines via a Combined Photooxidative Dearomatization‐Rearomatization Strategy</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2022-06-15</date><risdate>2022</risdate><volume>28</volume><issue>34</issue><spage>e202200309</spage><epage>n/a</epage><pages>e202200309-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The synthesis of arylamines from renewable resources under mild reaction conditions is highly desired for the sustainability of the chemical industry, where the production of hazardous waste is a prime concern. 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Two‐for‐one: Arylamines were obtained from biomass‐derived phenolic substrates and cyclic α‐amino acids by combining photooxidative dearomatization with decarboxylation/azomethine ylide chemistry. A novel organophotocatalytic approach was reported for the synthesis of a wide range of p‐quinols, including natural products and pharmaceutically‐relevant compounds.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>35393648</pmid><doi>10.1002/chem.202200309</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7234-8290</orcidid><orcidid>https://orcid.org/0000-0002-4541-6339</orcidid><orcidid>https://orcid.org/0000-0002-3859-8824</orcidid></addata></record> |
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subjects | Amines Amino acids arylamines Catalysts Chemical industry Chemistry Chemists dearomatization-rearomatization Hazardous wastes Natural products Organic compounds phenol-amine coupling Phenols photooxidation Renewable resources singlet oxygen Sustainability Sustainable yield |
title | A One‐Pot Approach for Bio‐Based Arylamines via a Combined Photooxidative Dearomatization‐Rearomatization Strategy |
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