Loading…

Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling

The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki−Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53−76% yiel...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2004-03, Vol.126 (12), p.3712-3713
Main Authors: Yamamoto, Yoshihiko, Ishii, Jun-ichi, Nishiyama, Hisao, Itoh, Kenji
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3
cites cdi_FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3
container_end_page 3713
container_issue 12
container_start_page 3712
container_title Journal of the American Chemical Society
container_volume 126
creator Yamamoto, Yoshihiko
Ishii, Jun-ichi
Nishiyama, Hisao
Itoh, Kenji
description The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki−Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53−76% yields.
doi_str_mv 10.1021/ja049673y
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71756690</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71756690</sourcerecordid><originalsourceid>FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3</originalsourceid><addsrcrecordid>eNptkc1y0zAUhT0MDE0LC16A0QamXbiVLP8oy-KhEAi0tClbjWJfxUpsKUhyB-cJWPNevARPgjrJpCy6utKcT_denRNFrwg-JTghZ0uB03Fe0OFJNCJZguOMJPnTaIQxTuKC5fQgOnRuGa5pwsjz6IBkmLKCpKPoz3V_PJmcxKXwoh02UKOygc7ESOgaXcNCGQctVF7dASqHqjXeqg6s2givjEZGolljAdCtdkPXQVAr0aLzdjVocMg31vSLBr0zNsAz6NbGCjuEk2_AnqJLDfGV8ejC9DYuTZA1aI9K069bpRfoTolHpp7d9Jt-pf7--v1FDaK3Yv_gRfRMitbBy109im4v3s_Kj_H08sOkPJ_GIk0zHzNJaV3gBJNkTnBOWKjAxnmdUZA4Z1IAITRhEsusJjKd02AqwyRnNaWikPQoervtu7bmRw_O8065CtpWaDC94wUpsjwf4wCebMHKGucsSL4OPwkWcIL5fXZ8n11gX--a9vMO6gdyF1YA3uwA4YLL0gpdKfcfl-MxK-65eMsp5-HnXhd2xcOgIuOzqxv-nX37TKefpvzrQ19ROb4MUejg3SML_gOeVMGk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71756690</pqid></control><display><type>article</type><title>Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Yamamoto, Yoshihiko ; Ishii, Jun-ichi ; Nishiyama, Hisao ; Itoh, Kenji</creator><creatorcontrib>Yamamoto, Yoshihiko ; Ishii, Jun-ichi ; Nishiyama, Hisao ; Itoh, Kenji</creatorcontrib><description>The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki−Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53−76% yields.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja049673y</identifier><identifier>PMID: 15038714</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemical reactivity ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Reactivity and mechanisms</subject><ispartof>Journal of the American Chemical Society, 2004-03, Vol.126 (12), p.3712-3713</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3</citedby><cites>FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=15609874$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15038714$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamamoto, Yoshihiko</creatorcontrib><creatorcontrib>Ishii, Jun-ichi</creatorcontrib><creatorcontrib>Nishiyama, Hisao</creatorcontrib><creatorcontrib>Itoh, Kenji</creatorcontrib><title>Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki−Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53−76% yields.</description><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptkc1y0zAUhT0MDE0LC16A0QamXbiVLP8oy-KhEAi0tClbjWJfxUpsKUhyB-cJWPNevARPgjrJpCy6utKcT_denRNFrwg-JTghZ0uB03Fe0OFJNCJZguOMJPnTaIQxTuKC5fQgOnRuGa5pwsjz6IBkmLKCpKPoz3V_PJmcxKXwoh02UKOygc7ESOgaXcNCGQctVF7dASqHqjXeqg6s2givjEZGolljAdCtdkPXQVAr0aLzdjVocMg31vSLBr0zNsAz6NbGCjuEk2_AnqJLDfGV8ejC9DYuTZA1aI9K069bpRfoTolHpp7d9Jt-pf7--v1FDaK3Yv_gRfRMitbBy109im4v3s_Kj_H08sOkPJ_GIk0zHzNJaV3gBJNkTnBOWKjAxnmdUZA4Z1IAITRhEsusJjKd02AqwyRnNaWikPQoervtu7bmRw_O8065CtpWaDC94wUpsjwf4wCebMHKGucsSL4OPwkWcIL5fXZ8n11gX--a9vMO6gdyF1YA3uwA4YLL0gpdKfcfl-MxK-65eMsp5-HnXhd2xcOgIuOzqxv-nX37TKefpvzrQ19ROb4MUejg3SML_gOeVMGk</recordid><startdate>20040331</startdate><enddate>20040331</enddate><creator>Yamamoto, Yoshihiko</creator><creator>Ishii, Jun-ichi</creator><creator>Nishiyama, Hisao</creator><creator>Itoh, Kenji</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040331</creationdate><title>Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling</title><author>Yamamoto, Yoshihiko ; Ishii, Jun-ichi ; Nishiyama, Hisao ; Itoh, Kenji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, Yoshihiko</creatorcontrib><creatorcontrib>Ishii, Jun-ichi</creatorcontrib><creatorcontrib>Nishiyama, Hisao</creatorcontrib><creatorcontrib>Itoh, Kenji</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamamoto, Yoshihiko</au><au>Ishii, Jun-ichi</au><au>Nishiyama, Hisao</au><au>Itoh, Kenji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2004-03-31</date><risdate>2004</risdate><volume>126</volume><issue>12</issue><spage>3712</spage><epage>3713</epage><pages>3712-3713</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The Ru(II)-catalyzed [2+2+2] cyclotrimerization of alkynylboronates, propargyl alcohol, and terminal alkynes proceeded chemo- and regioselectively to give rise to arylboronates, which were subjected to Suzuki−Miyaura cross-coupling with aryliodides to afford highly substituted biaryls in 53−76% yields.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15038714</pmid><doi>10.1021/ja049673y</doi><tpages>2</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2004-03, Vol.126 (12), p.3712-3713
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_71756690
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
title Ru(II)-Catalyzed Chemo- and Regioselective Cyclotrimerization of Three Unsymmetrical Alkynes through Boron Temporary Tether. One-Pot Four-Component Coupling via Cyclotrimerization/Suzuki−Miyaura Coupling
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T04%3A27%3A09IST&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=Ru(II)-Catalyzed%20Chemo-%20and%20Regioselective%20Cyclotrimerization%20of%20Three%20Unsymmetrical%20Alkynes%20through%20Boron%20Temporary%20Tether.%20One-Pot%20Four-Component%20Coupling%20via%20Cyclotrimerization/Suzuki%E2%88%92Miyaura%20Coupling&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Yamamoto,%20Yoshihiko&rft.date=2004-03-31&rft.volume=126&rft.issue=12&rft.spage=3712&rft.epage=3713&rft.pages=3712-3713&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja049673y&rft_dat=%3Cproquest_cross%3E71756690%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a445t-8f33d702012b1061812be896d53ef068fae11328f0f5d1f4b352080168d33a7f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=71756690&rft_id=info:pmid/15038714&rfr_iscdi=true