Synthesis of Ketones from α-Oxocarboxylates and Aryl Bromides by Cu/Pd-Catalyzed Decarboxylative Cross-Coupling

The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α‐oxocarboxylic acids and their cross‐coupling with aryl or heteroaryl bromides to give ketones. The reaction may be used in the presence...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie (International ed.) 2008-04, Vol.47 (16), p.3043-3045
Hauptverfasser: Gooßen, Lukas J, Rudolphi, Felix, Oppel, Christoph, Rodríguez, Nuria
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3045
container_issue 16
container_start_page 3043
container_title Angewandte Chemie (International ed.)
container_volume 47
creator Gooßen, Lukas J
Rudolphi, Felix
Oppel, Christoph
Rodríguez, Nuria
description The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α‐oxocarboxylic acids and their cross‐coupling with aryl or heteroaryl bromides to give ketones. The reaction may be used in the presence of many functional groups and provides good yields.
doi_str_mv 10.1002/anie.200705127
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_70482578</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>70482578</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4057-101d90f8eaf8a8d50f73247230419dab40317b5ee1365203c575701b22f7d7723</originalsourceid><addsrcrecordid>eNqF0M1u1DAUBeAIgWgpbFmCV-w8vbbj2LMc0h9aSgsqFagby0nsYsjEUzuBSd-KF-GZ8Cijlh0rW9Z3jqyTZS8JzAgA3dedMzMKIIATKh5lu4RTgpkQ7HG654xhITnZyZ7F-D15KaF4mu0QyaiQBd_NVpdj138z0UXkLXpvet-ZiGzwS_TnN75Y-1qHyq_HVvfpXXcNWoSxRW8TcE16qUZUDvsfG1zqXrfjnWnQgXnIuJ8GlcHHiEs_rFrX3TzPnljdRvNie-5lV0eHn8t3-Ozi-KRcnOE6By4wAdLMwUqjrdSy4WAFo7mgDHIyb3SVAyOi4sYQVnAKrOaCCyAVpVY0Irm97M3Uuwr-djCxV0sXa9O2ujN-iEpALikXMsHZBOvNP4OxahXcUodREVCbjdVmY3W_cQq82jYP1dI0D3w7agLzCfxyrRn_U6cW5yeH_5bjKetib9b3WR1-qEIwwdWX82N1cP2VnH6aX6sPyb-evNVe6Zvgorq6pEAYgJQ5LXL2F1Aroas</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>70482578</pqid></control><display><type>article</type><title>Synthesis of Ketones from α-Oxocarboxylates and Aryl Bromides by Cu/Pd-Catalyzed Decarboxylative Cross-Coupling</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Gooßen, Lukas J ; Rudolphi, Felix ; Oppel, Christoph ; Rodríguez, Nuria</creator><creatorcontrib>Gooßen, Lukas J ; Rudolphi, Felix ; Oppel, Christoph ; Rodríguez, Nuria</creatorcontrib><description>The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α‐oxocarboxylic acids and their cross‐coupling with aryl or heteroaryl bromides to give ketones. The reaction may be used in the presence of many functional groups and provides good yields.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200705127</identifier><identifier>PMID: 18327865</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>aryl ketones ; Bromides ; Carboxylic Acids ; Catalysis ; Copper ; cross-coupling ; Cross-Linking Reagents ; Decarboxylation ; homogeneous catalysis ; Ketones - chemical synthesis ; Palladium</subject><ispartof>Angewandte Chemie (International ed.), 2008-04, Vol.47 (16), p.3043-3045</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4057-101d90f8eaf8a8d50f73247230419dab40317b5ee1365203c575701b22f7d7723</citedby><cites>FETCH-LOGICAL-c4057-101d90f8eaf8a8d50f73247230419dab40317b5ee1365203c575701b22f7d7723</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.200705127$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.200705127$$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/18327865$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gooßen, Lukas J</creatorcontrib><creatorcontrib>Rudolphi, Felix</creatorcontrib><creatorcontrib>Oppel, Christoph</creatorcontrib><creatorcontrib>Rodríguez, Nuria</creatorcontrib><title>Synthesis of Ketones from α-Oxocarboxylates and Aryl Bromides by Cu/Pd-Catalyzed Decarboxylative Cross-Coupling</title><title>Angewandte Chemie (International ed.)</title><addtitle>Angewandte Chemie International Edition</addtitle><description>The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α‐oxocarboxylic acids and their cross‐coupling with aryl or heteroaryl bromides to give ketones. The reaction may be used in the presence of many functional groups and provides good yields.</description><subject>aryl ketones</subject><subject>Bromides</subject><subject>Carboxylic Acids</subject><subject>Catalysis</subject><subject>Copper</subject><subject>cross-coupling</subject><subject>Cross-Linking Reagents</subject><subject>Decarboxylation</subject><subject>homogeneous catalysis</subject><subject>Ketones - chemical synthesis</subject><subject>Palladium</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0M1u1DAUBeAIgWgpbFmCV-w8vbbj2LMc0h9aSgsqFagby0nsYsjEUzuBSd-KF-GZ8Cijlh0rW9Z3jqyTZS8JzAgA3dedMzMKIIATKh5lu4RTgpkQ7HG654xhITnZyZ7F-D15KaF4mu0QyaiQBd_NVpdj138z0UXkLXpvet-ZiGzwS_TnN75Y-1qHyq_HVvfpXXcNWoSxRW8TcE16qUZUDvsfG1zqXrfjnWnQgXnIuJ8GlcHHiEs_rFrX3TzPnljdRvNie-5lV0eHn8t3-Ozi-KRcnOE6By4wAdLMwUqjrdSy4WAFo7mgDHIyb3SVAyOi4sYQVnAKrOaCCyAVpVY0Irm97M3Uuwr-djCxV0sXa9O2ujN-iEpALikXMsHZBOvNP4OxahXcUodREVCbjdVmY3W_cQq82jYP1dI0D3w7agLzCfxyrRn_U6cW5yeH_5bjKetib9b3WR1-qEIwwdWX82N1cP2VnH6aX6sPyb-evNVe6Zvgorq6pEAYgJQ5LXL2F1Aroas</recordid><startdate>20080407</startdate><enddate>20080407</enddate><creator>Gooßen, Lukas J</creator><creator>Rudolphi, Felix</creator><creator>Oppel, Christoph</creator><creator>Rodríguez, Nuria</creator><general>Wiley-VCH Verlag</general><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><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>7X8</scope></search><sort><creationdate>20080407</creationdate><title>Synthesis of Ketones from α-Oxocarboxylates and Aryl Bromides by Cu/Pd-Catalyzed Decarboxylative Cross-Coupling</title><author>Gooßen, Lukas J ; Rudolphi, Felix ; Oppel, Christoph ; Rodríguez, Nuria</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4057-101d90f8eaf8a8d50f73247230419dab40317b5ee1365203c575701b22f7d7723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>aryl ketones</topic><topic>Bromides</topic><topic>Carboxylic Acids</topic><topic>Catalysis</topic><topic>Copper</topic><topic>cross-coupling</topic><topic>Cross-Linking Reagents</topic><topic>Decarboxylation</topic><topic>homogeneous catalysis</topic><topic>Ketones - chemical synthesis</topic><topic>Palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gooßen, Lukas J</creatorcontrib><creatorcontrib>Rudolphi, Felix</creatorcontrib><creatorcontrib>Oppel, Christoph</creatorcontrib><creatorcontrib>Rodríguez, Nuria</creatorcontrib><collection>AGRIS</collection><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>MEDLINE - Academic</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gooßen, Lukas J</au><au>Rudolphi, Felix</au><au>Oppel, Christoph</au><au>Rodríguez, Nuria</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Ketones from α-Oxocarboxylates and Aryl Bromides by Cu/Pd-Catalyzed Decarboxylative Cross-Coupling</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angewandte Chemie International Edition</addtitle><date>2008-04-07</date><risdate>2008</risdate><volume>47</volume><issue>16</issue><spage>3043</spage><epage>3045</epage><pages>3043-3045</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α‐oxocarboxylic acids and their cross‐coupling with aryl or heteroaryl bromides to give ketones. The reaction may be used in the presence of many functional groups and provides good yields.</abstract><cop>Weinheim</cop><pub>Wiley-VCH Verlag</pub><pmid>18327865</pmid><doi>10.1002/anie.200705127</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie (International ed.), 2008-04, Vol.47 (16), p.3043-3045
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_70482578
source MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects aryl ketones
Bromides
Carboxylic Acids
Catalysis
Copper
cross-coupling
Cross-Linking Reagents
Decarboxylation
homogeneous catalysis
Ketones - chemical synthesis
Palladium
title Synthesis of Ketones from α-Oxocarboxylates and Aryl Bromides by Cu/Pd-Catalyzed Decarboxylative Cross-Coupling
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-03T14%3A49%3A42IST&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=Synthesis%20of%20Ketones%20from%20%CE%B1-Oxocarboxylates%20and%20Aryl%20Bromides%20by%20Cu/Pd-Catalyzed%20Decarboxylative%20Cross-Coupling&rft.jtitle=Angewandte%20Chemie%20(International%20ed.)&rft.au=Goo%C3%9Fen,%20Lukas%20J&rft.date=2008-04-07&rft.volume=47&rft.issue=16&rft.spage=3043&rft.epage=3045&rft.pages=3043-3045&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.200705127&rft_dat=%3Cproquest_cross%3E70482578%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=70482578&rft_id=info:pmid/18327865&rfr_iscdi=true