Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water

Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water

Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2011-12, Vol.13 (24), p.6512-6515
Hauptverfasser: Hikawa, Hidemasa, Yokoyama, Yuusaku
Format: Artikel
Sprache:eng
Schlagworte:
Benzyl Alcohols - chemistry
Catalysis
Chemistry, Organic - methods
Molecular Structure
ortho-Aminobenzoates - chemistry
Palladium - chemistry
Water - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 6515
container_issue 24
container_start_page 6512
container_title Organic letters
container_volume 13
creator Hikawa, Hidemasa
Yokoyama, Yuusaku
description Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important roles for the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.
doi_str_mv 10.1021/ol2028042
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_911937331</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>911937331</sourcerecordid><originalsourceid>FETCH-LOGICAL-a314t-970383b91cd69eb9c5d9cf65b523c1911b663d17ce6064fd7108116644b8c3193</originalsourceid><addsrcrecordid>eNptkMtOwzAQRS0EouWx4AdQNgixCHjsxImXpeIlVYIFFTsix3FUV05cbEeo_XqMWrpiNaOZM1dzL0IXgG8BE7izhmBS4owcoDHkhKYFzsnhvmd4hE68X2IMccKP0YgQXBYF4WP0-SaMEY0eunQqgjDrjWqSe9Vv1kYEbfvEtsm8XzkblAxxNenDwoleGy2TidSNT751WOwukomRdmGNT3SffIig3Bk6aoXx6nxXT9H88eF9-pzOXp9eppNZKihkIeUFpiWtOciGcVVzmTdctiyvowEJHKBmjDZQSMUwy9qmAFwCMJZldSkpcHqKrre68dOvQflQddpLFa31yg6-ihKcFpRCJG-2pHTWe6faauV0J9y6Alz9plnt04zs5U51qDvV7Mm_-CJwtQWE9NXSDq6PJv8R-gEtJ3pk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>911937331</pqid></control><display><type>article</type><title>Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water</title><source>ACS Publications</source><source>MEDLINE</source><creator>Hikawa, Hidemasa ; Yokoyama, Yuusaku</creator><creatorcontrib>Hikawa, Hidemasa ; Yokoyama, Yuusaku</creatorcontrib><description>Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important roles for the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol2028042</identifier><identifier>PMID: 22087729</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Benzyl Alcohols - chemistry ; Catalysis ; Chemistry, Organic - methods ; Molecular Structure ; ortho-Aminobenzoates - chemistry ; Palladium - chemistry ; Water - chemistry</subject><ispartof>Organic letters, 2011-12, Vol.13 (24), p.6512-6515</ispartof><rights>Copyright © 2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a314t-970383b91cd69eb9c5d9cf65b523c1911b663d17ce6064fd7108116644b8c3193</citedby><cites>FETCH-LOGICAL-a314t-970383b91cd69eb9c5d9cf65b523c1911b663d17ce6064fd7108116644b8c3193</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol2028042$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol2028042$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22087729$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hikawa, Hidemasa</creatorcontrib><creatorcontrib>Yokoyama, Yuusaku</creatorcontrib><title>Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important roles for the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.</description><subject>Benzyl Alcohols - chemistry</subject><subject>Catalysis</subject><subject>Chemistry, Organic - methods</subject><subject>Molecular Structure</subject><subject>ortho-Aminobenzoates - chemistry</subject><subject>Palladium - chemistry</subject><subject>Water - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EouWx4AdQNgixCHjsxImXpeIlVYIFFTsix3FUV05cbEeo_XqMWrpiNaOZM1dzL0IXgG8BE7izhmBS4owcoDHkhKYFzsnhvmd4hE68X2IMccKP0YgQXBYF4WP0-SaMEY0eunQqgjDrjWqSe9Vv1kYEbfvEtsm8XzkblAxxNenDwoleGy2TidSNT751WOwukomRdmGNT3SffIig3Bk6aoXx6nxXT9H88eF9-pzOXp9eppNZKihkIeUFpiWtOciGcVVzmTdctiyvowEJHKBmjDZQSMUwy9qmAFwCMJZldSkpcHqKrre68dOvQflQddpLFa31yg6-ihKcFpRCJG-2pHTWe6faauV0J9y6Alz9plnt04zs5U51qDvV7Mm_-CJwtQWE9NXSDq6PJv8R-gEtJ3pk</recordid><startdate>20111216</startdate><enddate>20111216</enddate><creator>Hikawa, Hidemasa</creator><creator>Yokoyama, Yuusaku</creator><general>American Chemical Society</general><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>20111216</creationdate><title>Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water</title><author>Hikawa, Hidemasa ; Yokoyama, Yuusaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-970383b91cd69eb9c5d9cf65b523c1911b663d17ce6064fd7108116644b8c3193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Benzyl Alcohols - chemistry</topic><topic>Catalysis</topic><topic>Chemistry, Organic - methods</topic><topic>Molecular Structure</topic><topic>ortho-Aminobenzoates - chemistry</topic><topic>Palladium - chemistry</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hikawa, Hidemasa</creatorcontrib><creatorcontrib>Yokoyama, Yuusaku</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hikawa, Hidemasa</au><au>Yokoyama, Yuusaku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2011-12-16</date><risdate>2011</risdate><volume>13</volume><issue>24</issue><spage>6512</spage><epage>6515</epage><pages>6512-6515</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic acids in good yields. Water may play important roles for the smooth generation of the (η3-benzyl)palladium species by activation of the hydroxyl group of the benzyl alcohol.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22087729</pmid><doi>10.1021/ol2028042</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2011-12, Vol.13 (24), p.6512-6515
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_911937331
source ACS Publications; MEDLINE
subjects Benzyl Alcohols - chemistry
Catalysis
Chemistry, Organic - methods
Molecular Structure
ortho-Aminobenzoates - chemistry
Palladium - chemistry
Water - chemistry
title Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-15T19%3A39%3A22IST&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=Palladium-Catalyzed%20Benzylation%20of%20Unprotected%20Anthranilic%20Acids%20with%20Benzyl%20Alcohols%20in%20Water&rft.jtitle=Organic%20letters&rft.au=Hikawa,%20Hidemasa&rft.date=2011-12-16&rft.volume=13&rft.issue=24&rft.spage=6512&rft.epage=6515&rft.pages=6512-6515&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol2028042&rft_dat=%3Cproquest_cross%3E911937331%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=911937331&rft_id=info:pmid/22087729&rfr_iscdi=true