Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water

Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C–H bond oxidation functionalization does not require other oxidants and hydrogen acceptors, and H2 is the only byproduct. The oxyge...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2022-02, Vol.24 (5), p.1152-1157
Hauptverfasser: Zhang, Jin, Du, Jihong, Zhang, Chenyang, Liu, Kun, Yu, Feifei, Yuan, Yongkun, Duan, Baogen, Liu, Renhua
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1157
container_issue 5
container_start_page 1152
container_title Organic letters
container_volume 24
creator Zhang, Jin
Du, Jihong
Zhang, Chenyang
Liu, Kun
Yu, Feifei
Yuan, Yongkun
Duan, Baogen
Liu, Renhua
description Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C–H bond oxidation functionalization does not require other oxidants and hydrogen acceptors, and H2 is the only byproduct. The oxygen atom introduced into the products is confirmed to be from water by the MS analysis on the product of the 18O-labeled water reaction.
doi_str_mv 10.1021/acs.orglett.1c04154
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2624193722</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2624193722</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-5f7456ddc6c4e18600c982b3eecfada751ba2006b8b8f2a69b9640f481bf06823</originalsourceid><addsrcrecordid>eNp9kMtOwzAURC0EoqXwBUjISzZpbSd2kmWpeIlKXfBaRo5zQ1OSuNgOUL4eRy1dsrI1npl7fRA6p2RMCaMTqexYm7canBtTRSLKowM0pJyFQUw4O9zfBRmgE2tXhFCvpMdoEHKSpjQRQ_TyCDUoV30CXnxXhXSVbrEu8bR-39TSQAsWO43dEvDU6Ma_K_wATve6NvgK2h9ZF7DcFF74qtwSv0oH5hQdlbK2cLY7R-j55vppdhfMF7f3s-k8kGHEXcDLOOKiKJRQEfh9CFFpwvIQQJWykDGnuWSEiDzJk5JJkeapiEgZJTQviUhYOEKX29610R8dWJc1lVVQ17IF3dmMCRbRNIxZbw23VmW0tQbKbG2qRppNRknWA8080GwHNNsB9amL3YAub6DYZ_4IesNka-jTK92Z1v_338pfzeaFMw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2624193722</pqid></control><display><type>article</type><title>Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water</title><source>ACS Publications</source><creator>Zhang, Jin ; Du, Jihong ; Zhang, Chenyang ; Liu, Kun ; Yu, Feifei ; Yuan, Yongkun ; Duan, Baogen ; Liu, Renhua</creator><creatorcontrib>Zhang, Jin ; Du, Jihong ; Zhang, Chenyang ; Liu, Kun ; Yu, Feifei ; Yuan, Yongkun ; Duan, Baogen ; Liu, Renhua</creatorcontrib><description>Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C–H bond oxidation functionalization does not require other oxidants and hydrogen acceptors, and H2 is the only byproduct. The oxygen atom introduced into the products is confirmed to be from water by the MS analysis on the product of the 18O-labeled water reaction.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c04154</identifier><identifier>PMID: 35099186</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2022-02, Vol.24 (5), p.1152-1157</ispartof><rights>2022 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-5f7456ddc6c4e18600c982b3eecfada751ba2006b8b8f2a69b9640f481bf06823</citedby><cites>FETCH-LOGICAL-a345t-5f7456ddc6c4e18600c982b3eecfada751ba2006b8b8f2a69b9640f481bf06823</cites><orcidid>0000-0001-8253-6148</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.1c04154$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.1c04154$$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/35099186$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Jin</creatorcontrib><creatorcontrib>Du, Jihong</creatorcontrib><creatorcontrib>Zhang, Chenyang</creatorcontrib><creatorcontrib>Liu, Kun</creatorcontrib><creatorcontrib>Yu, Feifei</creatorcontrib><creatorcontrib>Yuan, Yongkun</creatorcontrib><creatorcontrib>Duan, Baogen</creatorcontrib><creatorcontrib>Liu, Renhua</creatorcontrib><title>Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C–H bond oxidation functionalization does not require other oxidants and hydrogen acceptors, and H2 is the only byproduct. The oxygen atom introduced into the products is confirmed to be from water by the MS analysis on the product of the 18O-labeled water reaction.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kMtOwzAURC0EoqXwBUjISzZpbSd2kmWpeIlKXfBaRo5zQ1OSuNgOUL4eRy1dsrI1npl7fRA6p2RMCaMTqexYm7canBtTRSLKowM0pJyFQUw4O9zfBRmgE2tXhFCvpMdoEHKSpjQRQ_TyCDUoV30CXnxXhXSVbrEu8bR-39TSQAsWO43dEvDU6Ma_K_wATve6NvgK2h9ZF7DcFF74qtwSv0oH5hQdlbK2cLY7R-j55vppdhfMF7f3s-k8kGHEXcDLOOKiKJRQEfh9CFFpwvIQQJWykDGnuWSEiDzJk5JJkeapiEgZJTQviUhYOEKX29610R8dWJc1lVVQ17IF3dmMCRbRNIxZbw23VmW0tQbKbG2qRppNRknWA8080GwHNNsB9amL3YAub6DYZ_4IesNka-jTK92Z1v_338pfzeaFMw</recordid><startdate>20220211</startdate><enddate>20220211</enddate><creator>Zhang, Jin</creator><creator>Du, Jihong</creator><creator>Zhang, Chenyang</creator><creator>Liu, Kun</creator><creator>Yu, Feifei</creator><creator>Yuan, Yongkun</creator><creator>Duan, Baogen</creator><creator>Liu, Renhua</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8253-6148</orcidid></search><sort><creationdate>20220211</creationdate><title>Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water</title><author>Zhang, Jin ; Du, Jihong ; Zhang, Chenyang ; Liu, Kun ; Yu, Feifei ; Yuan, Yongkun ; Duan, Baogen ; Liu, Renhua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-5f7456ddc6c4e18600c982b3eecfada751ba2006b8b8f2a69b9640f481bf06823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Jin</creatorcontrib><creatorcontrib>Du, Jihong</creatorcontrib><creatorcontrib>Zhang, Chenyang</creatorcontrib><creatorcontrib>Liu, Kun</creatorcontrib><creatorcontrib>Yu, Feifei</creatorcontrib><creatorcontrib>Yuan, Yongkun</creatorcontrib><creatorcontrib>Duan, Baogen</creatorcontrib><creatorcontrib>Liu, Renhua</creatorcontrib><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>Zhang, Jin</au><au>Du, Jihong</au><au>Zhang, Chenyang</au><au>Liu, Kun</au><au>Yu, Feifei</au><au>Yuan, Yongkun</au><au>Duan, Baogen</au><au>Liu, Renhua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2022-02-11</date><risdate>2022</risdate><volume>24</volume><issue>5</issue><spage>1152</spage><epage>1157</epage><pages>1152-1157</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes with water as the only oxygen donor is reported. This C–H bond oxidation functionalization does not require other oxidants and hydrogen acceptors, and H2 is the only byproduct. The oxygen atom introduced into the products is confirmed to be from water by the MS analysis on the product of the 18O-labeled water reaction.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>35099186</pmid><doi>10.1021/acs.orglett.1c04154</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8253-6148</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2022-02, Vol.24 (5), p.1152-1157
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2624193722
source ACS Publications
title Selective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T15%3A46%3A08IST&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=Selective%20Oxidation%20of%20Alkylarenes%20to%20the%20Aromatic%20Ketones%20or%20Benzaldehydes%20with%20Water&rft.jtitle=Organic%20letters&rft.au=Zhang,%20Jin&rft.date=2022-02-11&rft.volume=24&rft.issue=5&rft.spage=1152&rft.epage=1157&rft.pages=1152-1157&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c04154&rft_dat=%3Cproquest_cross%3E2624193722%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=2624193722&rft_id=info:pmid/35099186&rfr_iscdi=true