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,...
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Veröffentlicht in: | Journal of organic chemistry 2007-12, Vol.72 (26), p.10261-10263 |
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container_issue | 26 |
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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 |
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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> |
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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 |
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