Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bon...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:ACS catalysis 2017-07, Vol.7 (7), p.4491-4496
Hauptverfasser: Liu, Xiangqian, Jia, Jiaqi, Rueping, Magnus
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4496
container_issue 7
container_start_page 4491
container_title ACS catalysis
container_volume 7
creator Liu, Xiangqian
Jia, Jiaqi
Rueping, Magnus
description Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.
doi_str_mv 10.1021/acscatal.7b00941
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_acscatal_7b00941</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>i8910525</sourcerecordid><originalsourceid>FETCH-LOGICAL-a388t-2005757f5b65d84aff0f35556e898510814a4c6a359a14daa4e812f6719f69e73</originalsourceid><addsrcrecordid>eNp1kEFOwzAQRS0EElXpnqUPQIqd2InDroQWkAqVEKyjqWNTt25SxW6lsOoduCEnIaFFYsNsZqT_38zoI3RJyZCSkF6DdBI82GEyJyRl9AT1Qsp5wFnET__M52jg3JK0xXgsEtJD-2cjV8oGWYc3H6rA2df-c4Zvq7IIMqtgZ8p3PLKrxoI3VYkrjcfOq9rd4DtTK-nxi9pYkGqtSt-pfqEODvxUGeUbPG_wZFvKjgZruhM_63C2AFO6C3SmwTo1OPY-epuMX7OHYDq7f8xG0wAiIXwQEsITnmg-j3khGGhNdMQ5j5VIBadEUAZMxhDxFCgrAJgSNNRxQlMdpyqJ-ogc9sq6cq5WOt_UZg11k1OSdyHmvyHmxxBb5OqAtEq-rLZ1-7_73_4NUuN3Fw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains</title><source>American Chemical Society Journals</source><creator>Liu, Xiangqian ; Jia, Jiaqi ; Rueping, Magnus</creator><creatorcontrib>Liu, Xiangqian ; Jia, Jiaqi ; Rueping, Magnus</creatorcontrib><description>Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.</description><identifier>ISSN: 2155-5435</identifier><identifier>EISSN: 2155-5435</identifier><identifier>DOI: 10.1021/acscatal.7b00941</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>ACS catalysis, 2017-07, Vol.7 (7), p.4491-4496</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a388t-2005757f5b65d84aff0f35556e898510814a4c6a359a14daa4e812f6719f69e73</citedby><cites>FETCH-LOGICAL-a388t-2005757f5b65d84aff0f35556e898510814a4c6a359a14daa4e812f6719f69e73</cites><orcidid>0000-0003-4580-5227</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/acscatal.7b00941$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acscatal.7b00941$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Liu, Xiangqian</creatorcontrib><creatorcontrib>Jia, Jiaqi</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><title>Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains</title><title>ACS catalysis</title><addtitle>ACS Catal</addtitle><description>Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.</description><issn>2155-5435</issn><issn>2155-5435</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kEFOwzAQRS0EElXpnqUPQIqd2InDroQWkAqVEKyjqWNTt25SxW6lsOoduCEnIaFFYsNsZqT_38zoI3RJyZCSkF6DdBI82GEyJyRl9AT1Qsp5wFnET__M52jg3JK0xXgsEtJD-2cjV8oGWYc3H6rA2df-c4Zvq7IIMqtgZ8p3PLKrxoI3VYkrjcfOq9rd4DtTK-nxi9pYkGqtSt-pfqEODvxUGeUbPG_wZFvKjgZruhM_63C2AFO6C3SmwTo1OPY-epuMX7OHYDq7f8xG0wAiIXwQEsITnmg-j3khGGhNdMQ5j5VIBadEUAZMxhDxFCgrAJgSNNRxQlMdpyqJ-ogc9sq6cq5WOt_UZg11k1OSdyHmvyHmxxBb5OqAtEq-rLZ1-7_73_4NUuN3Fw</recordid><startdate>20170707</startdate><enddate>20170707</enddate><creator>Liu, Xiangqian</creator><creator>Jia, Jiaqi</creator><creator>Rueping, Magnus</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-4580-5227</orcidid></search><sort><creationdate>20170707</creationdate><title>Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains</title><author>Liu, Xiangqian ; Jia, Jiaqi ; Rueping, Magnus</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a388t-2005757f5b65d84aff0f35556e898510814a4c6a359a14daa4e812f6719f69e73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Xiangqian</creatorcontrib><creatorcontrib>Jia, Jiaqi</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><collection>CrossRef</collection><jtitle>ACS catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Xiangqian</au><au>Jia, Jiaqi</au><au>Rueping, Magnus</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains</atitle><jtitle>ACS catalysis</jtitle><addtitle>ACS Catal</addtitle><date>2017-07-07</date><risdate>2017</risdate><volume>7</volume><issue>7</issue><spage>4491</spage><epage>4496</epage><pages>4491-4496</pages><issn>2155-5435</issn><eissn>2155-5435</eissn><abstract>Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.</abstract><pub>American Chemical Society</pub><doi>10.1021/acscatal.7b00941</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-4580-5227</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 2155-5435
ispartof ACS catalysis, 2017-07, Vol.7 (7), p.4491-4496
issn 2155-5435
2155-5435
language eng
recordid cdi_crossref_primary_10_1021_acscatal_7b00941
source American Chemical Society Journals
title Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T08%3A23%3A50IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Nickel-Catalyzed%20C%E2%80%93O%20Bond-Cleaving%20Alkylation%20of%20Esters:%20Direct%20Replacement%20of%20the%20Ester%20Moiety%20by%20Functionalized%20Alkyl%20Chains&rft.jtitle=ACS%20catalysis&rft.au=Liu,%20Xiangqian&rft.date=2017-07-07&rft.volume=7&rft.issue=7&rft.spage=4491&rft.epage=4496&rft.pages=4491-4496&rft.issn=2155-5435&rft.eissn=2155-5435&rft_id=info:doi/10.1021/acscatal.7b00941&rft_dat=%3Cacs_cross%3Ei8910525%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true