A Highly Regioselective Synthesis of Polysubstituted Naphthalene Derivatives through Gallium Trichloride Catalyzed Alkyne-Aldehyde Coupling
A convenient synthesis of polysubstituted naphthalenes 3 involves the gallium trichloride catalyzed coupling of aromatic alkynes 1 and phenyl acetaldehydes or ketones 2 in dichloromethane. The reaction is highly regioselective.
Gespeichert in:
Veröffentlicht in: | Angewandte Chemie International Edition 2002-06, Vol.41 (12), p.2138-2141 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 2141 |
---|---|
container_issue | 12 |
container_start_page | 2138 |
container_title | Angewandte Chemie International Edition |
container_volume | 41 |
creator | Viswanathan, Ganapathy S. Wang, Mingwen Li, Chao-Jun |
description | A convenient synthesis of polysubstituted naphthalenes 3 involves the gallium trichloride catalyzed coupling of aromatic alkynes 1 and phenyl acetaldehydes or ketones 2 in dichloromethane. The reaction is highly regioselective. |
doi_str_mv | 10.1002/1521-3773(20020617)41:12<2138::AID-ANIE2138>3.0.CO;2-T |
format | Article |
fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_72933474</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72933474</sourcerecordid><originalsourceid>FETCH-LOGICAL-i3298-6439726b4c89a5cdeb52ead9e72e92be19b62d9b6a8a84cedf2bc74e9d3ef2043</originalsourceid><addsrcrecordid>eNpFkd1u00AQhS0EoqXwCmivEFw4eH_itQOqZNySRIoSBEFIcDFa25N4240dvOuC-wp9aWylCTc7OzPnnIv5PO-SBiMaBOw9HTPqcyn5W9a3QUjlO0EnlH1klEeTSTK_8pPl_HroLvkoGKWrD8xfP_HOT8an_V9w7stoTM-8F9be9EFRFITPvTMaSxGGjJ57DwmZ6W1pOvIVt7q2aDB3-g7Jt65yJVptSb0hX2rT2TazTrvWYUGWal-6UhmskFxho-_U4LHElU3dbksyVcbodkfWjc5LUze6QJIqp0x337sTc9tV6CemwLIbNnW7N7ravvSebZSx-OqxXnjfP1-v05m_WE3nabLwNWdx5IeCx5KFmcijWI3zArMxQ1XEKBnGLEMaZyEr-kdFKhI5FhuW5VJgXHDcsEDwC-_NIXff1L9btA522uZojKqwbi1IFnMu5CB8_Shssx0WsG_0TjUdHM_XC34dBH-0we7_PoABIgwsYGABR4ggKFAGAzboGcKRIXAIIF0Bg_Vp1qf7h3RtHf49pavmFkLJ5Rh-LKcwk58WP8WUQsj_AThApyk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72933474</pqid></control><display><type>article</type><title>A Highly Regioselective Synthesis of Polysubstituted Naphthalene Derivatives through Gallium Trichloride Catalyzed Alkyne-Aldehyde Coupling</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Viswanathan, Ganapathy S. ; Wang, Mingwen ; Li, Chao-Jun</creator><creatorcontrib>Viswanathan, Ganapathy S. ; Wang, Mingwen ; Li, Chao-Jun</creatorcontrib><description>A convenient synthesis of polysubstituted naphthalenes 3 involves the gallium trichloride catalyzed coupling of aromatic alkynes 1 and phenyl acetaldehydes or ketones 2 in dichloromethane. The reaction is highly regioselective.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/1521-3773(20020617)41:12<2138::AID-ANIE2138>3.0.CO;2-T</identifier><identifier>PMID: 19746621</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><subject>aldehydes ; Aldehydes - chemistry ; alkynes ; Alkynes - chemistry ; Catalysis ; Chlorides - chemistry ; gallium ; Gallium - chemistry ; Molecular Structure ; naphthalenes ; Naphthols - chemistry ; Solvents - chemistry ; Stereoisomerism ; synthetic methods ; Temperature</subject><ispartof>Angewandte Chemie International Edition, 2002-06, Vol.41 (12), p.2138-2141</ispartof><rights>2002 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2F1521-3773%2820020617%2941%3A12%3C2138%3A%3AAID-ANIE2138%3E3.0.CO%3B2-T$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2F1521-3773%2820020617%2941%3A12%3C2138%3A%3AAID-ANIE2138%3E3.0.CO%3B2-T$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19746621$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Viswanathan, Ganapathy S.</creatorcontrib><creatorcontrib>Wang, Mingwen</creatorcontrib><creatorcontrib>Li, Chao-Jun</creatorcontrib><title>A Highly Regioselective Synthesis of Polysubstituted Naphthalene Derivatives through Gallium Trichloride Catalyzed Alkyne-Aldehyde Coupling</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A convenient synthesis of polysubstituted naphthalenes 3 involves the gallium trichloride catalyzed coupling of aromatic alkynes 1 and phenyl acetaldehydes or ketones 2 in dichloromethane. The reaction is highly regioselective.</description><subject>aldehydes</subject><subject>Aldehydes - chemistry</subject><subject>alkynes</subject><subject>Alkynes - chemistry</subject><subject>Catalysis</subject><subject>Chlorides - chemistry</subject><subject>gallium</subject><subject>Gallium - chemistry</subject><subject>Molecular Structure</subject><subject>naphthalenes</subject><subject>Naphthols - chemistry</subject><subject>Solvents - chemistry</subject><subject>Stereoisomerism</subject><subject>synthetic methods</subject><subject>Temperature</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkd1u00AQhS0EoqXwCmivEFw4eH_itQOqZNySRIoSBEFIcDFa25N4240dvOuC-wp9aWylCTc7OzPnnIv5PO-SBiMaBOw9HTPqcyn5W9a3QUjlO0EnlH1klEeTSTK_8pPl_HroLvkoGKWrD8xfP_HOT8an_V9w7stoTM-8F9be9EFRFITPvTMaSxGGjJ57DwmZ6W1pOvIVt7q2aDB3-g7Jt65yJVptSb0hX2rT2TazTrvWYUGWal-6UhmskFxho-_U4LHElU3dbksyVcbodkfWjc5LUze6QJIqp0x337sTc9tV6CemwLIbNnW7N7ravvSebZSx-OqxXnjfP1-v05m_WE3nabLwNWdx5IeCx5KFmcijWI3zArMxQ1XEKBnGLEMaZyEr-kdFKhI5FhuW5VJgXHDcsEDwC-_NIXff1L9btA522uZojKqwbi1IFnMu5CB8_Shssx0WsG_0TjUdHM_XC34dBH-0we7_PoABIgwsYGABR4ggKFAGAzboGcKRIXAIIF0Bg_Vp1qf7h3RtHf49pavmFkLJ5Rh-LKcwk58WP8WUQsj_AThApyk</recordid><startdate>20020617</startdate><enddate>20020617</enddate><creator>Viswanathan, Ganapathy S.</creator><creator>Wang, Mingwen</creator><creator>Li, Chao-Jun</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20020617</creationdate><title>A Highly Regioselective Synthesis of Polysubstituted Naphthalene Derivatives through Gallium Trichloride Catalyzed Alkyne-Aldehyde Coupling</title><author>Viswanathan, Ganapathy S. ; Wang, Mingwen ; Li, Chao-Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i3298-6439726b4c89a5cdeb52ead9e72e92be19b62d9b6a8a84cedf2bc74e9d3ef2043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>aldehydes</topic><topic>Aldehydes - chemistry</topic><topic>alkynes</topic><topic>Alkynes - chemistry</topic><topic>Catalysis</topic><topic>Chlorides - chemistry</topic><topic>gallium</topic><topic>Gallium - chemistry</topic><topic>Molecular Structure</topic><topic>naphthalenes</topic><topic>Naphthols - chemistry</topic><topic>Solvents - chemistry</topic><topic>Stereoisomerism</topic><topic>synthetic methods</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Viswanathan, Ganapathy S.</creatorcontrib><creatorcontrib>Wang, Mingwen</creatorcontrib><creatorcontrib>Li, Chao-Jun</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Viswanathan, Ganapathy S.</au><au>Wang, Mingwen</au><au>Li, Chao-Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Highly Regioselective Synthesis of Polysubstituted Naphthalene Derivatives through Gallium Trichloride Catalyzed Alkyne-Aldehyde Coupling</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2002-06-17</date><risdate>2002</risdate><volume>41</volume><issue>12</issue><spage>2138</spage><epage>2141</epage><pages>2138-2141</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A convenient synthesis of polysubstituted naphthalenes 3 involves the gallium trichloride catalyzed coupling of aromatic alkynes 1 and phenyl acetaldehydes or ketones 2 in dichloromethane. The reaction is highly regioselective.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><pmid>19746621</pmid><doi>10.1002/1521-3773(20020617)41:12<2138::AID-ANIE2138>3.0.CO;2-T</doi><tpages>4</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1433-7851 |
ispartof | Angewandte Chemie International Edition, 2002-06, Vol.41 (12), p.2138-2141 |
issn | 1433-7851 1521-3773 |
language | eng |
recordid | cdi_proquest_miscellaneous_72933474 |
source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
subjects | aldehydes Aldehydes - chemistry alkynes Alkynes - chemistry Catalysis Chlorides - chemistry gallium Gallium - chemistry Molecular Structure naphthalenes Naphthols - chemistry Solvents - chemistry Stereoisomerism synthetic methods Temperature |
title | A Highly Regioselective Synthesis of Polysubstituted Naphthalene Derivatives through Gallium Trichloride Catalyzed Alkyne-Aldehyde Coupling |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-15T11%3A43%3A53IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Highly%20Regioselective%20Synthesis%20of%20Polysubstituted%20Naphthalene%20Derivatives%20through%20Gallium%20Trichloride%20Catalyzed%20Alkyne-Aldehyde%20Coupling&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Viswanathan,%20Ganapathy%20S.&rft.date=2002-06-17&rft.volume=41&rft.issue=12&rft.spage=2138&rft.epage=2141&rft.pages=2138-2141&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/1521-3773(20020617)41:12%3C2138::AID-ANIE2138%3E3.0.CO;2-T&rft_dat=%3Cproquest_pubme%3E72933474%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=72933474&rft_id=info:pmid/19746621&rfr_iscdi=true |