First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes

First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes

1,4-Hydrosilylation of dienes catalyzed by late transition metals constitutes a straightforward access to allylsilanes. However, when unsymmetric dienes are used, it generally leads to a mixture of regioisomers (tail or head products) via Z-specific 1,4-addition. Here we describe the first catalytic...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organometallics 2005-11, Vol.24 (24), p.5802-5806
Hauptverfasser: Bareille, Laurianne, Becht, Sabine, Cui, Jin Lan, Le Gendre, Pierre, Moïse, Claude
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5806
container_issue 24
container_start_page 5802
container_title Organometallics
container_volume 24
creator Bareille, Laurianne
Becht, Sabine
Cui, Jin Lan
Le Gendre, Pierre
Moïse, Claude
description 1,4-Hydrosilylation of dienes catalyzed by late transition metals constitutes a straightforward access to allylsilanes. However, when unsymmetric dienes are used, it generally leads to a mixture of regioisomers (tail or head products) via Z-specific 1,4-addition. Here we describe the first catalytic anti-1,4-hydrosilylation of dienes using the cheap and stable Cp2TiF2 complex as catalyst. It affords E-allylsilanes in good to excellent yields with an unprecedented regio- and diastereoselectivity. Dehydrogenative double silylation of dienes can be selectively obtained by simply changing the activation protocol of the precatalyst.
doi_str_mv 10.1021/om050533m
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_om050533m</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c886226641</sourcerecordid><originalsourceid>FETCH-LOGICAL-a104m-a68041c145fd994772e294533839d7217fa3e894d9b2599a56881ea87ed300793</originalsourceid><addsrcrecordid>eNptj81KxDAYRYMoWEcXvkE3LgQzfvlrEnAjHccZGHAzrstnk0KG_kjSWdSntzLiytXdHC7nEHLLYMmAs8ehAwVKiO6MZExxoAVIdk4y4LqgWghxSa5SOgBAoQXPyNM6xDTm-zBiH44dLXHEdvryLse8HwNlD5JuJheHFNqpxTEMfT40-Sr43qdrctFgm_zN7y7I-_plX27o7u11Wz7vKDKQHcXCzBI1k6px1kqtuedWzpJGWKc50w0Kb6x09oMra1EVxjCPRnsnALQVC3J_-q1njxR9U33G0GGcKgbVT3b1lz2zdycW61QdhmPsZ7N_uG-GZVQX</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes</title><source>American Chemical Society Journals</source><creator>Bareille, Laurianne ; Becht, Sabine ; Cui, Jin Lan ; Le Gendre, Pierre ; Moïse, Claude</creator><creatorcontrib>Bareille, Laurianne ; Becht, Sabine ; Cui, Jin Lan ; Le Gendre, Pierre ; Moïse, Claude</creatorcontrib><description>1,4-Hydrosilylation of dienes catalyzed by late transition metals constitutes a straightforward access to allylsilanes. However, when unsymmetric dienes are used, it generally leads to a mixture of regioisomers (tail or head products) via Z-specific 1,4-addition. Here we describe the first catalytic anti-1,4-hydrosilylation of dienes using the cheap and stable Cp2TiF2 complex as catalyst. It affords E-allylsilanes in good to excellent yields with an unprecedented regio- and diastereoselectivity. Dehydrogenative double silylation of dienes can be selectively obtained by simply changing the activation protocol of the precatalyst.</description><identifier>ISSN: 0276-7333</identifier><identifier>EISSN: 1520-6041</identifier><identifier>DOI: 10.1021/om050533m</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organometallics, 2005-11, Vol.24 (24), p.5802-5806</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a104m-a68041c145fd994772e294533839d7217fa3e894d9b2599a56881ea87ed300793</citedby><cites>FETCH-LOGICAL-a104m-a68041c145fd994772e294533839d7217fa3e894d9b2599a56881ea87ed300793</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/om050533m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/om050533m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Bareille, Laurianne</creatorcontrib><creatorcontrib>Becht, Sabine</creatorcontrib><creatorcontrib>Cui, Jin Lan</creatorcontrib><creatorcontrib>Le Gendre, Pierre</creatorcontrib><creatorcontrib>Moïse, Claude</creatorcontrib><title>First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes</title><title>Organometallics</title><addtitle>Organometallics</addtitle><description>1,4-Hydrosilylation of dienes catalyzed by late transition metals constitutes a straightforward access to allylsilanes. However, when unsymmetric dienes are used, it generally leads to a mixture of regioisomers (tail or head products) via Z-specific 1,4-addition. Here we describe the first catalytic anti-1,4-hydrosilylation of dienes using the cheap and stable Cp2TiF2 complex as catalyst. It affords E-allylsilanes in good to excellent yields with an unprecedented regio- and diastereoselectivity. Dehydrogenative double silylation of dienes can be selectively obtained by simply changing the activation protocol of the precatalyst.</description><issn>0276-7333</issn><issn>1520-6041</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptj81KxDAYRYMoWEcXvkE3LgQzfvlrEnAjHccZGHAzrstnk0KG_kjSWdSntzLiytXdHC7nEHLLYMmAs8ehAwVKiO6MZExxoAVIdk4y4LqgWghxSa5SOgBAoQXPyNM6xDTm-zBiH44dLXHEdvryLse8HwNlD5JuJheHFNqpxTEMfT40-Sr43qdrctFgm_zN7y7I-_plX27o7u11Wz7vKDKQHcXCzBI1k6px1kqtuedWzpJGWKc50w0Kb6x09oMra1EVxjCPRnsnALQVC3J_-q1njxR9U33G0GGcKgbVT3b1lz2zdycW61QdhmPsZ7N_uG-GZVQX</recordid><startdate>20051121</startdate><enddate>20051121</enddate><creator>Bareille, Laurianne</creator><creator>Becht, Sabine</creator><creator>Cui, Jin Lan</creator><creator>Le Gendre, Pierre</creator><creator>Moïse, Claude</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20051121</creationdate><title>First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes</title><author>Bareille, Laurianne ; Becht, Sabine ; Cui, Jin Lan ; Le Gendre, Pierre ; Moïse, Claude</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a104m-a68041c145fd994772e294533839d7217fa3e894d9b2599a56881ea87ed300793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bareille, Laurianne</creatorcontrib><creatorcontrib>Becht, Sabine</creatorcontrib><creatorcontrib>Cui, Jin Lan</creatorcontrib><creatorcontrib>Le Gendre, Pierre</creatorcontrib><creatorcontrib>Moïse, Claude</creatorcontrib><collection>CrossRef</collection><jtitle>Organometallics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bareille, Laurianne</au><au>Becht, Sabine</au><au>Cui, Jin Lan</au><au>Le Gendre, Pierre</au><au>Moïse, Claude</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes</atitle><jtitle>Organometallics</jtitle><addtitle>Organometallics</addtitle><date>2005-11-21</date><risdate>2005</risdate><volume>24</volume><issue>24</issue><spage>5802</spage><epage>5806</epage><pages>5802-5806</pages><issn>0276-7333</issn><eissn>1520-6041</eissn><abstract>1,4-Hydrosilylation of dienes catalyzed by late transition metals constitutes a straightforward access to allylsilanes. However, when unsymmetric dienes are used, it generally leads to a mixture of regioisomers (tail or head products) via Z-specific 1,4-addition. Here we describe the first catalytic anti-1,4-hydrosilylation of dienes using the cheap and stable Cp2TiF2 complex as catalyst. It affords E-allylsilanes in good to excellent yields with an unprecedented regio- and diastereoselectivity. Dehydrogenative double silylation of dienes can be selectively obtained by simply changing the activation protocol of the precatalyst.</abstract><pub>American Chemical Society</pub><doi>10.1021/om050533m</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0276-7333
ispartof Organometallics, 2005-11, Vol.24 (24), p.5802-5806
issn 0276-7333
1520-6041
language eng
recordid cdi_crossref_primary_10_1021_om050533m
source American Chemical Society Journals
title First Titanium-Catalyzed a nti-1,4-Hydrosilylation of Dienes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-24T14%3A41%3A31IST&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=First%20Titanium-Catalyzed%20a%20nti-1,4-Hydrosilylation%20of%20Dienes&rft.jtitle=Organometallics&rft.au=Bareille,%20Laurianne&rft.date=2005-11-21&rft.volume=24&rft.issue=24&rft.spage=5802&rft.epage=5806&rft.pages=5802-5806&rft.issn=0276-7333&rft.eissn=1520-6041&rft_id=info:doi/10.1021/om050533m&rft_dat=%3Cacs_cross%3Ec886226641%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