Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes

Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes

We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring,...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2005-03, Vol.127 (12), p.4186-4187
Hauptverfasser: Lian, Jian-Jou, Odedra, Arjan, Wu, Chang-Jung, Liu, Rai-Shung
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4187
container_issue 12
container_start_page 4186
container_title Journal of the American Chemical Society
container_volume 127
creator Lian, Jian-Jou
Odedra, Arjan
Wu, Chang-Jung
Liu, Rai-Shung
description We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring, in addition to a regiocontrolled 1,2-alkyl migration. This cyclization provides an easy and convenient synthesis of complex benzenes bearing various different substituents.
doi_str_mv 10.1021/ja0504901
format Article
fullrecord <record><control><sourceid>istex_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_ja0504901</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ark_67375_TPS_65JBMGHW_1</sourcerecordid><originalsourceid>FETCH-LOGICAL-a327t-d0b21aa61f2f70af307dd5b85b44427510996df7cb993417c6e1bcecd3987e483</originalsourceid><addsrcrecordid>eNptUE1v00AQtRBIhMKBf7AXDki47Ie9a3NLotKAWhU1QRyt8e44cXDX1e661D0hcYErv4R_wn_oL-lWQYEDp5nRvHnvzUuS54weMsrZ6y3QnGYlZQ-SCcs5TXPG5cNkQinlqSqkeJw88X4bx4wXbJL8Oh_CBm07XKRzCNCNN2jIOa7b3mOHOrRXSNgrkZ5i2IwdWiQrB9Y36Eg9knmHcAVrJH1DVl96MjVb0GgD-f0t0rm6t7fff-4aMuut8W9uv_4gU0uOwI8ErCHLvcpytNGJb_092aJdb7qRLIfat2EI0dMM7U2U90-TRw10Hp_9qQfJx7dHq_kiPTk7fjefnqQguAqpoTVnAJI1vFEUGkGVMXld5HWWZVzljJalNI3SdVmKjCktkdUatRFloTArxEHycserXe-9w6a6dO0FuLFitLqPutpHHbEvdthL8Bq6JiakW__3QEqRSSoiLt3hWh_wer8H97mSSqi8Wn1YVjJ_Pzs9Xnyq_uEF7attPzgbP_6P_h2sJZ0p</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes</title><source>American Chemical Society Journals</source><creator>Lian, Jian-Jou ; Odedra, Arjan ; Wu, Chang-Jung ; Liu, Rai-Shung</creator><creatorcontrib>Lian, Jian-Jou ; Odedra, Arjan ; Wu, Chang-Jung ; Liu, Rai-Shung</creatorcontrib><description>We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring, in addition to a regiocontrolled 1,2-alkyl migration. This cyclization provides an easy and convenient synthesis of complex benzenes bearing various different substituents.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0504901</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, 2005-03, Vol.127 (12), p.4186-4187</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a327t-d0b21aa61f2f70af307dd5b85b44427510996df7cb993417c6e1bcecd3987e483</citedby><cites>FETCH-LOGICAL-a327t-d0b21aa61f2f70af307dd5b85b44427510996df7cb993417c6e1bcecd3987e483</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/ja0504901$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0504901$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=16634603$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Lian, Jian-Jou</creatorcontrib><creatorcontrib>Odedra, Arjan</creatorcontrib><creatorcontrib>Wu, Chang-Jung</creatorcontrib><creatorcontrib>Liu, Rai-Shung</creatorcontrib><title>Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring, in addition to a regiocontrolled 1,2-alkyl migration. This cyclization provides an easy and convenient synthesis of complex benzenes bearing various different substituents.</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>2005</creationdate><recordtype>article</recordtype><recordid>eNptUE1v00AQtRBIhMKBf7AXDki47Ie9a3NLotKAWhU1QRyt8e44cXDX1e661D0hcYErv4R_wn_oL-lWQYEDp5nRvHnvzUuS54weMsrZ6y3QnGYlZQ-SCcs5TXPG5cNkQinlqSqkeJw88X4bx4wXbJL8Oh_CBm07XKRzCNCNN2jIOa7b3mOHOrRXSNgrkZ5i2IwdWiQrB9Y36Eg9knmHcAVrJH1DVl96MjVb0GgD-f0t0rm6t7fff-4aMuut8W9uv_4gU0uOwI8ErCHLvcpytNGJb_092aJdb7qRLIfat2EI0dMM7U2U90-TRw10Hp_9qQfJx7dHq_kiPTk7fjefnqQguAqpoTVnAJI1vFEUGkGVMXld5HWWZVzljJalNI3SdVmKjCktkdUatRFloTArxEHycserXe-9w6a6dO0FuLFitLqPutpHHbEvdthL8Bq6JiakW__3QEqRSSoiLt3hWh_wer8H97mSSqi8Wn1YVjJ_Pzs9Xnyq_uEF7attPzgbP_6P_h2sJZ0p</recordid><startdate>20050330</startdate><enddate>20050330</enddate><creator>Lian, Jian-Jou</creator><creator>Odedra, Arjan</creator><creator>Wu, Chang-Jung</creator><creator>Liu, Rai-Shung</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20050330</creationdate><title>Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes</title><author>Lian, Jian-Jou ; Odedra, Arjan ; Wu, Chang-Jung ; Liu, Rai-Shung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a327t-d0b21aa61f2f70af307dd5b85b44427510996df7cb993417c6e1bcecd3987e483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</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>Lian, Jian-Jou</creatorcontrib><creatorcontrib>Odedra, Arjan</creatorcontrib><creatorcontrib>Wu, Chang-Jung</creatorcontrib><creatorcontrib>Liu, Rai-Shung</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lian, Jian-Jou</au><au>Odedra, Arjan</au><au>Wu, Chang-Jung</au><au>Liu, Rai-Shung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2005-03-30</date><risdate>2005</risdate><volume>127</volume><issue>12</issue><spage>4186</spage><epage>4187</epage><pages>4186-4187</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring, in addition to a regiocontrolled 1,2-alkyl migration. This cyclization provides an easy and convenient synthesis of complex benzenes bearing various different substituents.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ja0504901</doi><tpages>2</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2005-03, Vol.127 (12), p.4186-4187
issn 0002-7863
1520-5126
language eng
recordid cdi_crossref_primary_10_1021_ja0504901
source American Chemical Society Journals
subjects Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
title Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds:  An Easy and Selective Synthesis of Highly Subsituted Benzenes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-01T01%3A00%3A03IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-istex_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Ruthenium-Catalyzed%20Regioselective%201,3-Methylene%20Transfer%20by%20Cleavage%20of%20Two%20Adjacent%20%CF%83-Carbon%E2%88%92Carbon%20Bonds:%E2%80%89%20An%20Easy%20and%20Selective%20Synthesis%20of%20Highly%20Subsituted%20Benzenes&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Lian,%20Jian-Jou&rft.date=2005-03-30&rft.volume=127&rft.issue=12&rft.spage=4186&rft.epage=4187&rft.pages=4186-4187&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja0504901&rft_dat=%3Cistex_cross%3Eark_67375_TPS_65JBMGHW_1%3C/istex_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