The Decarboxylative Blaise Reaction

Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided β-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent,...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2007-12, Vol.72 (26), p.10261-10263
Hauptverfasser: Lee, Jae Hoon, Choi, Bo Seung, Chang, Jay Hyok, Lee, Hee Bong, Yoon, Joo-Yong, Lee, Jaeick, Shin, Hyunik
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 10263
container_issue 26
container_start_page 10261
container_title Journal of organic chemistry
container_volume 72
creator Lee, Jae Hoon
Choi, Bo Seung
Chang, Jay Hyok
Lee, Hee Bong
Yoon, Joo-Yong
Lee, Jaeick
Shin, Hyunik
description Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided β-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent, and is possible with 0.5−1.0 equiv of zinc chloride.
doi_str_mv 10.1021/jo701743m
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_69061045</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>69061045</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-edc4c6c956cbfd4a5c79e0aebca4fd1ea3346837f5e949b678814454eba54d653</originalsourceid><addsrcrecordid>eNpt0MtOwzAQBVALgWgpLPgBVAmBxCJgx48kSyhQHpV4tLC1Js5EpKRJsRPU_j2pGrUbvJmFj65mLiHHjF4y6rOraRlQFgg-2yFdJn3qqYiKXdKl1Pc97iveIQfOTWnzpJT7pMNCKgIesC45nXxh_xYN2LhcLHOosl_s3-SQOey_I5gqK4tDspdC7vConT3ycX83GTx4o5fh4-B65AEPWeVhYoRRJpLKxGkiQJogQgoYGxBpwhA4FyrkQSoxElGsgjBkQkiBMUiRKMl75HydO7flT42u0rPMGcxzKLCsnW6uUoyKFbxYQ2NL5yymem6zGdilZlSvGtGbRhp70obW8QyTrWwraMBZC8AZyFMLhcnc1kWRoD6njfPWLnMVLjb_YL-1aoKknryO9dPz-PNtyAdabHPBuGaf2hZNd_8s-AeFAoI8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>69061045</pqid></control><display><type>article</type><title>The Decarboxylative Blaise Reaction</title><source>MEDLINE</source><source>ACS Publications</source><creator>Lee, Jae Hoon ; Choi, Bo Seung ; Chang, Jay Hyok ; Lee, Hee Bong ; Yoon, Joo-Yong ; Lee, Jaeick ; Shin, Hyunik</creator><creatorcontrib>Lee, Jae Hoon ; Choi, Bo Seung ; Chang, Jay Hyok ; Lee, Hee Bong ; Yoon, Joo-Yong ; Lee, Jaeick ; Shin, Hyunik</creatorcontrib><description>Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided β-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent, and is possible with 0.5−1.0 equiv of zinc chloride.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo701743m</identifier><identifier>PMID: 18047371</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acrylates - chemical synthesis ; Acrylates - chemistry ; Aliphatic compounds ; Catalysis ; Chemistry ; Chlorides - chemistry ; Decarboxylation ; Exact sciences and technology ; Malonates - chemistry ; Molecular Structure ; Nitriles - chemistry ; Organic chemistry ; Potassium - chemistry ; Preparations and properties ; Solvents - chemistry ; Zinc Compounds - chemistry</subject><ispartof>Journal of organic chemistry, 2007-12, Vol.72 (26), p.10261-10263</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-edc4c6c956cbfd4a5c79e0aebca4fd1ea3346837f5e949b678814454eba54d653</citedby><cites>FETCH-LOGICAL-a381t-edc4c6c956cbfd4a5c79e0aebca4fd1ea3346837f5e949b678814454eba54d653</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/jo701743m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo701743m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=19940230$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18047371$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Jae Hoon</creatorcontrib><creatorcontrib>Choi, Bo Seung</creatorcontrib><creatorcontrib>Chang, Jay Hyok</creatorcontrib><creatorcontrib>Lee, Hee Bong</creatorcontrib><creatorcontrib>Yoon, Joo-Yong</creatorcontrib><creatorcontrib>Lee, Jaeick</creatorcontrib><creatorcontrib>Shin, Hyunik</creatorcontrib><title>The Decarboxylative Blaise Reaction</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided β-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent, and is possible with 0.5−1.0 equiv of zinc chloride.</description><subject>Acrylates - chemical synthesis</subject><subject>Acrylates - chemistry</subject><subject>Aliphatic compounds</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Chlorides - chemistry</subject><subject>Decarboxylation</subject><subject>Exact sciences and technology</subject><subject>Malonates - chemistry</subject><subject>Molecular Structure</subject><subject>Nitriles - chemistry</subject><subject>Organic chemistry</subject><subject>Potassium - chemistry</subject><subject>Preparations and properties</subject><subject>Solvents - chemistry</subject><subject>Zinc Compounds - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtOwzAQBVALgWgpLPgBVAmBxCJgx48kSyhQHpV4tLC1Js5EpKRJsRPU_j2pGrUbvJmFj65mLiHHjF4y6rOraRlQFgg-2yFdJn3qqYiKXdKl1Pc97iveIQfOTWnzpJT7pMNCKgIesC45nXxh_xYN2LhcLHOosl_s3-SQOey_I5gqK4tDspdC7vConT3ycX83GTx4o5fh4-B65AEPWeVhYoRRJpLKxGkiQJogQgoYGxBpwhA4FyrkQSoxElGsgjBkQkiBMUiRKMl75HydO7flT42u0rPMGcxzKLCsnW6uUoyKFbxYQ2NL5yymem6zGdilZlSvGtGbRhp70obW8QyTrWwraMBZC8AZyFMLhcnc1kWRoD6njfPWLnMVLjb_YL-1aoKknryO9dPz-PNtyAdabHPBuGaf2hZNd_8s-AeFAoI8</recordid><startdate>20071221</startdate><enddate>20071221</enddate><creator>Lee, Jae Hoon</creator><creator>Choi, Bo Seung</creator><creator>Chang, Jay Hyok</creator><creator>Lee, Hee Bong</creator><creator>Yoon, Joo-Yong</creator><creator>Lee, Jaeick</creator><creator>Shin, Hyunik</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20071221</creationdate><title>The Decarboxylative Blaise Reaction</title><author>Lee, Jae Hoon ; Choi, Bo Seung ; Chang, Jay Hyok ; Lee, Hee Bong ; Yoon, Joo-Yong ; Lee, Jaeick ; Shin, Hyunik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-edc4c6c956cbfd4a5c79e0aebca4fd1ea3346837f5e949b678814454eba54d653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Acrylates - chemical synthesis</topic><topic>Acrylates - chemistry</topic><topic>Aliphatic compounds</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Chlorides - chemistry</topic><topic>Decarboxylation</topic><topic>Exact sciences and technology</topic><topic>Malonates - chemistry</topic><topic>Molecular Structure</topic><topic>Nitriles - chemistry</topic><topic>Organic chemistry</topic><topic>Potassium - chemistry</topic><topic>Preparations and properties</topic><topic>Solvents - chemistry</topic><topic>Zinc Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Jae Hoon</creatorcontrib><creatorcontrib>Choi, Bo Seung</creatorcontrib><creatorcontrib>Chang, Jay Hyok</creatorcontrib><creatorcontrib>Lee, Hee Bong</creatorcontrib><creatorcontrib>Yoon, Joo-Yong</creatorcontrib><creatorcontrib>Lee, Jaeick</creatorcontrib><creatorcontrib>Shin, Hyunik</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Jae Hoon</au><au>Choi, Bo Seung</au><au>Chang, Jay Hyok</au><au>Lee, Hee Bong</au><au>Yoon, Joo-Yong</au><au>Lee, Jaeick</au><au>Shin, Hyunik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Decarboxylative Blaise Reaction</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2007-12-21</date><risdate>2007</risdate><volume>72</volume><issue>26</issue><spage>10261</spage><epage>10263</epage><pages>10261-10263</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Reaction of aryl nitriles with potassium ethyl malonate in the presence of zinc chloride and a catalytic amount of Hünig's base provided β-amino acrylates in moderate to good yield. Compared to the classical Blaise reaction, this reaction is safer (endothermic), devoid of lachrymatory reagent, and is possible with 0.5−1.0 equiv of zinc chloride.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18047371</pmid><doi>10.1021/jo701743m</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2007-12, Vol.72 (26), p.10261-10263
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_69061045
source MEDLINE; ACS Publications
subjects Acrylates - chemical synthesis
Acrylates - chemistry
Aliphatic compounds
Catalysis
Chemistry
Chlorides - chemistry
Decarboxylation
Exact sciences and technology
Malonates - chemistry
Molecular Structure
Nitriles - chemistry
Organic chemistry
Potassium - chemistry
Preparations and properties
Solvents - chemistry
Zinc Compounds - chemistry
title The Decarboxylative Blaise Reaction
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-24T03%3A26%3A56IST&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=The%20Decarboxylative%20Blaise%20Reaction&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Lee,%20Jae%20Hoon&rft.date=2007-12-21&rft.volume=72&rft.issue=26&rft.spage=10261&rft.epage=10263&rft.pages=10261-10263&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo701743m&rft_dat=%3Cproquest_cross%3E69061045%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=69061045&rft_id=info:pmid/18047371&rfr_iscdi=true