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Copper-catalyzed synthesis of primary amides through reductive N-O cleavage of dioxazolones
A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction...
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Published in: | RSC advances 2024-03, Vol.14 (14), p.944-9444 |
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creator | Bae, Hyeonwoong Park, Jinhwan Yoon, Rahyun Lee, Seunghoon Son, Jongwoo |
description | A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction conditions allow the transformation of dioxazolones to primary amides, in which sensitive functional groups such as hydroxyl, aldehyde, trialkylsilyl, and unsaturated carbon units are tolerated with excellent chemoselectivity.
Reaction of dioxazolones in the presence of a copper catalyst and a silane is represented. Mild reductive reaction conditions for the N-O bond cleavage and large-scale protocols are also highlighted with excellent tolerance in the presence of water. |
doi_str_mv | 10.1039/d4ra00320a |
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Reaction of dioxazolones in the presence of a copper catalyst and a silane is represented. Mild reductive reaction conditions for the N-O bond cleavage and large-scale protocols are also highlighted with excellent tolerance in the presence of water.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d4ra00320a</identifier><identifier>PMID: 38516159</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Amides ; Chemical synthesis ; Chemistry ; Copper ; Functional groups</subject><ispartof>RSC advances, 2024-03, Vol.14 (14), p.944-9444</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2024</rights><rights>This journal is © The Royal Society of Chemistry 2024 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c388t-c7813bb1a38c2d8eabf100b93b18aa71c1f33713007fe0454f8c0a68c6ff8243</cites><orcidid>0000-0001-9447-4503 ; 0000-0003-0420-5065</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10951817/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10951817/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,315,733,786,790,891,27957,27958,53827,53829</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38516159$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bae, Hyeonwoong</creatorcontrib><creatorcontrib>Park, Jinhwan</creatorcontrib><creatorcontrib>Yoon, Rahyun</creatorcontrib><creatorcontrib>Lee, Seunghoon</creatorcontrib><creatorcontrib>Son, Jongwoo</creatorcontrib><title>Copper-catalyzed synthesis of primary amides through reductive N-O cleavage of dioxazolones</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction conditions allow the transformation of dioxazolones to primary amides, in which sensitive functional groups such as hydroxyl, aldehyde, trialkylsilyl, and unsaturated carbon units are tolerated with excellent chemoselectivity.
Reaction of dioxazolones in the presence of a copper catalyst and a silane is represented. Mild reductive reaction conditions for the N-O bond cleavage and large-scale protocols are also highlighted with excellent tolerance in the presence of water.</description><subject>Aldehydes</subject><subject>Amides</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Copper</subject><subject>Functional groups</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkc1rFEEQxRtRTIi5eFcGvARhTFX3fPScZFmjCYQEJDcPTU1P9e6E2em1e2Zx89dn4q5rtC5VUL96vOIJ8RbhE4KqzpssEICSQC_EsYSsSCUU1ctn85E4jfEepipylAW-FkdK51hgXh2LH3O_XnNILQ3UbR-4SeK2H5Yc25h4l6xDu6KwTWjVNhyTYRn8uFgmgZvRDu2Gk5v0NrEd04YW_HTQtP4XPfjO9xzfiFeOusin-34i7r5e3M0v0-vbb1fz2XVqldZDakuNqq6RlLay0Uy1Q4C6UjVqohItOqVKVAClY8jyzGkLVGhbOKdlpk7E553seqxX3Fjuh0Cd2Vs3nlrz76Zvl2bhNwahylFjOSmc7RWC_zlyHMyqjZa7jnr2YzSyKjMAKVU1oR_-Q-_9GPrpPaNAQYl5AWqiPu4oG3yMgd3BDYJ5is18yb7Pfsc2m-D3z_0f0D8hTcC7HRCiPWz_5q4eAWoenTw</recordid><startdate>20240320</startdate><enddate>20240320</enddate><creator>Bae, Hyeonwoong</creator><creator>Park, Jinhwan</creator><creator>Yoon, Rahyun</creator><creator>Lee, Seunghoon</creator><creator>Son, Jongwoo</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0001-9447-4503</orcidid><orcidid>https://orcid.org/0000-0003-0420-5065</orcidid></search><sort><creationdate>20240320</creationdate><title>Copper-catalyzed synthesis of primary amides through reductive N-O cleavage of dioxazolones</title><author>Bae, Hyeonwoong ; Park, Jinhwan ; Yoon, Rahyun ; Lee, Seunghoon ; Son, Jongwoo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c388t-c7813bb1a38c2d8eabf100b93b18aa71c1f33713007fe0454f8c0a68c6ff8243</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Aldehydes</topic><topic>Amides</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Copper</topic><topic>Functional groups</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bae, Hyeonwoong</creatorcontrib><creatorcontrib>Park, Jinhwan</creatorcontrib><creatorcontrib>Yoon, Rahyun</creatorcontrib><creatorcontrib>Lee, Seunghoon</creatorcontrib><creatorcontrib>Son, Jongwoo</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>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bae, Hyeonwoong</au><au>Park, Jinhwan</au><au>Yoon, Rahyun</au><au>Lee, Seunghoon</au><au>Son, Jongwoo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed synthesis of primary amides through reductive N-O cleavage of dioxazolones</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2024-03-20</date><risdate>2024</risdate><volume>14</volume><issue>14</issue><spage>944</spage><epage>9444</epage><pages>944-9444</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><notes>https://doi.org/10.1039/d4ra00320a</notes><notes>Electronic supplementary information (ESI) available. See DOI</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A new method for the synthesis of primary amides is developed, in which dioxazolones are treated with a copper catalyst under mild reaction conditions. A broad scope of dioxazolones is exhibited as well as dioxazolones containing biologically active structural motifs. These robust and mild reaction conditions allow the transformation of dioxazolones to primary amides, in which sensitive functional groups such as hydroxyl, aldehyde, trialkylsilyl, and unsaturated carbon units are tolerated with excellent chemoselectivity.
Reaction of dioxazolones in the presence of a copper catalyst and a silane is represented. Mild reductive reaction conditions for the N-O bond cleavage and large-scale protocols are also highlighted with excellent tolerance in the presence of water.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38516159</pmid><doi>10.1039/d4ra00320a</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-9447-4503</orcidid><orcidid>https://orcid.org/0000-0003-0420-5065</orcidid><oa>free_for_read</oa></addata></record> |
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source | Open Access: PubMed Central |
subjects | Aldehydes Amides Chemical synthesis Chemistry Copper Functional groups |
title | Copper-catalyzed synthesis of primary amides through reductive N-O cleavage of dioxazolones |
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