Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity

Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity

Lewis acid complexes of the type [M{(R)-BINAP}][SbF6]2 (M = Pt, Pd, Ni) catalyze the reaction between α-methylstyrenes and ethyl trifluoropyruvate to afford products resulting from the expected carbonyl-ene reactivity as well as tandem alkene dimerization−carbonyl-ene addition and alkene dimerizatio...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organometallics 2007-11, Vol.26 (24), p.5961-5966
Hauptverfasser: Doherty, Simon, Knight, Julian G, Smyth, Catherine H, Harrington, Ross W, Clegg, William
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5966
container_issue 24
container_start_page 5961
container_title Organometallics
container_volume 26
creator Doherty, Simon
Knight, Julian G
Smyth, Catherine H
Harrington, Ross W
Clegg, William
description Lewis acid complexes of the type [M{(R)-BINAP}][SbF6]2 (M = Pt, Pd, Ni) catalyze the reaction between α-methylstyrenes and ethyl trifluoropyruvate to afford products resulting from the expected carbonyl-ene reactivity as well as tandem alkene dimerization−carbonyl-ene addition and alkene dimerization−Friedel−Crafts alkylation pathways, the distribution of which depends on the metal and the substituent attached to the aromatic ring of the styrene substrate. Kinetic studies reveal that the Lewis acid platinum complex catalyzes the dimerization of 4-chloro-α-methylstyrene much faster than its palladium counterpart and that the corresponding nickel system has platinum-like reactivity and selectivity.
doi_str_mv 10.1021/om7006612
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_om7006612</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>b42738118</sourcerecordid><originalsourceid>FETCH-LOGICAL-a297t-c2d7303a5194f87f562096989bc395220194d5a5bb7148e7df0f94ca86ca2f093</originalsourceid><addsrcrecordid>eNptkM9uEzEQhy1EJULhwBv4wgGJLbY3u85yi7bpHylVqxKExMVyvGPh1muvbKewPXGEK4_Eo_RJcJqqXHoaafTNNzM_hN5QckAJox98zwmpa8qeoQmtGClqMqXP0YQwXhe8LMsX6GWMVyRDvGQT9PcMkrTFIQzgOnAJX4JUydyYNGKv8cKCSsEP34w1Cl9YmYzb9Pg4-M2A70fxEr6biOfKdLiVuTHGFD_e_fyNW98PkEyWAZ7ba3CAD00Pwdxmi3fv8alLQfY-r9hYGfBRMNCBvfv1pw1Sp7gdGu0DK91WH9bejbZYZNX_O1-hPS1thNcPdR99Plqs2pNieX582s6XhWQNT4ViHS9JKSvaTPWM66pmpKmbWbNWZVMxRnK_q2S1XnM6nQHvNNHNVMlZrSTTpCn30budVwUfYwAthmB6GUZBidiGLx7Dz2yxY01M8OMRlOFa5Nx5JVYXn8SKnVRfLs9W4mvm3-54qaK48pvg8idPeP8BlmOX8g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity</title><source>ACS Publications</source><creator>Doherty, Simon ; Knight, Julian G ; Smyth, Catherine H ; Harrington, Ross W ; Clegg, William</creator><creatorcontrib>Doherty, Simon ; Knight, Julian G ; Smyth, Catherine H ; Harrington, Ross W ; Clegg, William</creatorcontrib><description>Lewis acid complexes of the type [M{(R)-BINAP}][SbF6]2 (M = Pt, Pd, Ni) catalyze the reaction between α-methylstyrenes and ethyl trifluoropyruvate to afford products resulting from the expected carbonyl-ene reactivity as well as tandem alkene dimerization−carbonyl-ene addition and alkene dimerization−Friedel−Crafts alkylation pathways, the distribution of which depends on the metal and the substituent attached to the aromatic ring of the styrene substrate. Kinetic studies reveal that the Lewis acid platinum complex catalyzes the dimerization of 4-chloro-α-methylstyrene much faster than its palladium counterpart and that the corresponding nickel system has platinum-like reactivity and selectivity.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/om7006612</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organometallics, 2007-11, Vol.26 (24), p.5961-5966</ispartof><rights>Copyright © 2007 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a297t-c2d7303a5194f87f562096989bc395220194d5a5bb7148e7df0f94ca86ca2f093</citedby><cites>FETCH-LOGICAL-a297t-c2d7303a5194f87f562096989bc395220194d5a5bb7148e7df0f94ca86ca2f093</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/om7006612$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/om7006612$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids></links><search><creatorcontrib>Doherty, Simon</creatorcontrib><creatorcontrib>Knight, Julian G</creatorcontrib><creatorcontrib>Smyth, Catherine H</creatorcontrib><creatorcontrib>Harrington, Ross W</creatorcontrib><creatorcontrib>Clegg, William</creatorcontrib><title>Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity</title><title>Organometallics</title><addtitle>Organometallics</addtitle><description>Lewis acid complexes of the type [M{(R)-BINAP}][SbF6]2 (M = Pt, Pd, Ni) catalyze the reaction between α-methylstyrenes and ethyl trifluoropyruvate to afford products resulting from the expected carbonyl-ene reactivity as well as tandem alkene dimerization−carbonyl-ene addition and alkene dimerization−Friedel−Crafts alkylation pathways, the distribution of which depends on the metal and the substituent attached to the aromatic ring of the styrene substrate. Kinetic studies reveal that the Lewis acid platinum complex catalyzes the dimerization of 4-chloro-α-methylstyrene much faster than its palladium counterpart and that the corresponding nickel system has platinum-like reactivity and selectivity.</description><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNptkM9uEzEQhy1EJULhwBv4wgGJLbY3u85yi7bpHylVqxKExMVyvGPh1muvbKewPXGEK4_Eo_RJcJqqXHoaafTNNzM_hN5QckAJox98zwmpa8qeoQmtGClqMqXP0YQwXhe8LMsX6GWMVyRDvGQT9PcMkrTFIQzgOnAJX4JUydyYNGKv8cKCSsEP34w1Cl9YmYzb9Pg4-M2A70fxEr6biOfKdLiVuTHGFD_e_fyNW98PkEyWAZ7ba3CAD00Pwdxmi3fv8alLQfY-r9hYGfBRMNCBvfv1pw1Sp7gdGu0DK91WH9bejbZYZNX_O1-hPS1thNcPdR99Plqs2pNieX582s6XhWQNT4ViHS9JKSvaTPWM66pmpKmbWbNWZVMxRnK_q2S1XnM6nQHvNNHNVMlZrSTTpCn30budVwUfYwAthmB6GUZBidiGLx7Dz2yxY01M8OMRlOFa5Nx5JVYXn8SKnVRfLs9W4mvm3-54qaK48pvg8idPeP8BlmOX8g</recordid><startdate>20071119</startdate><enddate>20071119</enddate><creator>Doherty, Simon</creator><creator>Knight, Julian G</creator><creator>Smyth, Catherine H</creator><creator>Harrington, Ross W</creator><creator>Clegg, William</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20071119</creationdate><title>Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity</title><author>Doherty, Simon ; Knight, Julian G ; Smyth, Catherine H ; Harrington, Ross W ; Clegg, William</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a297t-c2d7303a5194f87f562096989bc395220194d5a5bb7148e7df0f94ca86ca2f093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Doherty, Simon</creatorcontrib><creatorcontrib>Knight, Julian G</creatorcontrib><creatorcontrib>Smyth, Catherine H</creatorcontrib><creatorcontrib>Harrington, Ross W</creatorcontrib><creatorcontrib>Clegg, William</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Doherty, Simon</au><au>Knight, Julian G</au><au>Smyth, Catherine H</au><au>Harrington, Ross W</au><au>Clegg, William</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity</atitle><jtitle>Organometallics</jtitle><addtitle>Organometallics</addtitle><date>2007-11-19</date><risdate>2007</risdate><volume>26</volume><issue>24</issue><spage>5961</spage><epage>5966</epage><pages>5961-5966</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>Lewis acid complexes of the type [M{(R)-BINAP}][SbF6]2 (M = Pt, Pd, Ni) catalyze the reaction between α-methylstyrenes and ethyl trifluoropyruvate to afford products resulting from the expected carbonyl-ene reactivity as well as tandem alkene dimerization−carbonyl-ene addition and alkene dimerization−Friedel−Crafts alkylation pathways, the distribution of which depends on the metal and the substituent attached to the aromatic ring of the styrene substrate. Kinetic studies reveal that the Lewis acid platinum complex catalyzes the dimerization of 4-chloro-α-methylstyrene much faster than its palladium counterpart and that the corresponding nickel system has platinum-like reactivity and selectivity.</abstract><pub>American Chemical Society</pub><doi>10.1021/om7006612</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0276-7333
ispartof Organometallics, 2007-11, Vol.26 (24), p.5961-5966
issn 0276-7333
1520-6041
language eng
recordid cdi_crossref_primary_10_1021_om7006612
source ACS Publications
title Metal-Dependent Reactivity of Electrophilic Platinum Group Metal Lewis Acid Catalysts:  Competitive Alkene Dimerization, Intramolecular Friedel−Crafts Alkylation, and Carbonyl-Ene Reactivity
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T19%3A46%3A48IST&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=Metal-Dependent%20Reactivity%20of%20Electrophilic%20Platinum%20Group%20Metal%20Lewis%20Acid%20Catalysts:%E2%80%89%20Competitive%20Alkene%20Dimerization,%20Intramolecular%20Friedel%E2%88%92Crafts%20Alkylation,%20and%20Carbonyl-Ene%20Reactivity&rft.jtitle=Organometallics&rft.au=Doherty,%20Simon&rft.date=2007-11-19&rft.volume=26&rft.issue=24&rft.spage=5961&rft.epage=5966&rft.pages=5961-5966&rft.issn=0276-7333&rft.eissn=1520-6041&rft_id=info:doi/10.1021/om7006612&rft_dat=%3Cacs_cross%3Eb42738118%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