Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst

Metal‐free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2012-02, Vol.51 (6), p.1383-1386
Hauptverfasser: Allen, C. Liana, Atkinson, Benjamin N., Williams, Jonathan M. J.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1386
container_issue 6
container_start_page 1383
container_title Angewandte Chemie International Edition
container_volume 51
creator Allen, C. Liana
Atkinson, Benjamin N.
Williams, Jonathan M. J.
description Metal‐free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen‐bonding complex is proposed.
doi_str_mv 10.1002/anie.201107348
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_919648445</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>919648445</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4438-2e82314cf1b7bf0500dd771205d5ee0d66acadf705966dd978bd2cab48ff9b373</originalsourceid><addsrcrecordid>eNqFkUtv1DAUhSMEog_YskSRWNBNBl8_Ymc5mrbTkYaCqlaV2FhO7ExdMnaxM2rz7-soZYRYwMrHV985su_Jsg-AZoAQ_qKcNTOMABAnVLzKDoFhKAjn5HXSlJCCCwYH2VGM94kXApVvswOMMRDA4jDbXAflotparXrrXe7b_HuwWxWGfJ6GJuaPtr8btUv6Jlq3yS8GHfzT0KlxON2au86HhOcq5srlK-fDJj2tyReqV90Q-3fZm1Z10bx_OY-zm_Oz68VFsf62XC3m66KhlIgCG4EJ0KaFmtctYghpzTlgxDQzBumyVI3SLUesKkutKy5qjRtVU9G2VU04Oc4-T7kPwf_amdjLrY2N6TrljN9FWUFVUkEpS-TJP0ngaauY0AoS-ukv9N7vgkv_kMCg5IiiagycTVQTfIzBtPJh2qQEJMey5FiW3JeVDB9fYnf11ug9_rudBFQT8Gg7M_wnTs4vV2d_hheT18bePO29KvyUJSecydvLpVye_oDTNb2SX8kzQrSv8w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1516704095</pqid></control><display><type>article</type><title>Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Allen, C. Liana ; Atkinson, Benjamin N. ; Williams, Jonathan M. J.</creator><creatorcontrib>Allen, C. Liana ; Atkinson, Benjamin N. ; Williams, Jonathan M. J.</creatorcontrib><description>Metal‐free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen‐bonding complex is proposed.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201107348</identifier><identifier>PMID: 22213128</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Amides ; Amides - chemical synthesis ; Amides - chemistry ; Amines ; Amines - chemistry ; Catalysis ; Catalysts ; Hydrochlorides ; Hydroxylamine - chemistry ; hydroxylamines ; Magnetic Resonance Spectroscopy ; metal-free catalysis ; primary amides ; transamidation</subject><ispartof>Angewandte Chemie International Edition, 2012-02, Vol.51 (6), p.1383-1386</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4438-2e82314cf1b7bf0500dd771205d5ee0d66acadf705966dd978bd2cab48ff9b373</citedby><cites>FETCH-LOGICAL-c4438-2e82314cf1b7bf0500dd771205d5ee0d66acadf705966dd978bd2cab48ff9b373</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.201107348$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201107348$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22213128$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Allen, C. Liana</creatorcontrib><creatorcontrib>Atkinson, Benjamin N.</creatorcontrib><creatorcontrib>Williams, Jonathan M. J.</creatorcontrib><title>Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Metal‐free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen‐bonding complex is proposed.</description><subject>Activation</subject><subject>Amides</subject><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Amines</subject><subject>Amines - chemistry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Hydrochlorides</subject><subject>Hydroxylamine - chemistry</subject><subject>hydroxylamines</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>metal-free catalysis</subject><subject>primary amides</subject><subject>transamidation</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUtv1DAUhSMEog_YskSRWNBNBl8_Ymc5mrbTkYaCqlaV2FhO7ExdMnaxM2rz7-soZYRYwMrHV985su_Jsg-AZoAQ_qKcNTOMABAnVLzKDoFhKAjn5HXSlJCCCwYH2VGM94kXApVvswOMMRDA4jDbXAflotparXrrXe7b_HuwWxWGfJ6GJuaPtr8btUv6Jlq3yS8GHfzT0KlxON2au86HhOcq5srlK-fDJj2tyReqV90Q-3fZm1Z10bx_OY-zm_Oz68VFsf62XC3m66KhlIgCG4EJ0KaFmtctYghpzTlgxDQzBumyVI3SLUesKkutKy5qjRtVU9G2VU04Oc4-T7kPwf_amdjLrY2N6TrljN9FWUFVUkEpS-TJP0ngaauY0AoS-ukv9N7vgkv_kMCg5IiiagycTVQTfIzBtPJh2qQEJMey5FiW3JeVDB9fYnf11ug9_rudBFQT8Gg7M_wnTs4vV2d_hheT18bePO29KvyUJSecydvLpVye_oDTNb2SX8kzQrSv8w</recordid><startdate>20120206</startdate><enddate>20120206</enddate><creator>Allen, C. Liana</creator><creator>Atkinson, Benjamin N.</creator><creator>Williams, Jonathan M. J.</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope></search><sort><creationdate>20120206</creationdate><title>Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst</title><author>Allen, C. Liana ; Atkinson, Benjamin N. ; Williams, Jonathan M. J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4438-2e82314cf1b7bf0500dd771205d5ee0d66acadf705966dd978bd2cab48ff9b373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Activation</topic><topic>Amides</topic><topic>Amides - chemical synthesis</topic><topic>Amides - chemistry</topic><topic>Amines</topic><topic>Amines - chemistry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Hydrochlorides</topic><topic>Hydroxylamine - chemistry</topic><topic>hydroxylamines</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>metal-free catalysis</topic><topic>primary amides</topic><topic>transamidation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Allen, C. Liana</creatorcontrib><creatorcontrib>Atkinson, Benjamin N.</creatorcontrib><creatorcontrib>Williams, Jonathan M. J.</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 &amp; Medical Complete (Alumni)</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Allen, C. Liana</au><au>Atkinson, Benjamin N.</au><au>Williams, Jonathan M. J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2012-02-06</date><risdate>2012</risdate><volume>51</volume><issue>6</issue><spage>1383</spage><epage>1386</epage><pages>1383-1386</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Metal‐free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen‐bonding complex is proposed.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>22213128</pmid><doi>10.1002/anie.201107348</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie International Edition, 2012-02, Vol.51 (6), p.1383-1386
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_919648445
source MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects Activation
Amides
Amides - chemical synthesis
Amides - chemistry
Amines
Amines - chemistry
Catalysis
Catalysts
Hydrochlorides
Hydroxylamine - chemistry
hydroxylamines
Magnetic Resonance Spectroscopy
metal-free catalysis
primary amides
transamidation
title Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T02%3A50%3A23IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Transamidation%20of%20Primary%20Amides%20with%20Amines%20Using%20Hydroxylamine%20Hydrochloride%20as%20an%20Inorganic%20Catalyst&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Allen,%20C.%20Liana&rft.date=2012-02-06&rft.volume=51&rft.issue=6&rft.spage=1383&rft.epage=1386&rft.pages=1383-1386&rft.issn=1433-7851&rft.eissn=1521-3773&rft.coden=ACIEAY&rft_id=info:doi/10.1002/anie.201107348&rft_dat=%3Cproquest_cross%3E919648445%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1516704095&rft_id=info:pmid/22213128&rfr_iscdi=true