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Amino acid-promoted Ullmann-type coupling reactions and their applications in organic synthesis
Ullmann-type coupling reactions between aryl halides and N-containing reagents, phenols, and other related nucleophilic agents are very valuable transformations for organic synthesis. Their conventional reaction conditions require high reaction temperatures. We describe here that some amino acids, e...
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Published in: | Pure and applied chemistry 2009-01, Vol.81 (2), p.227-234 |
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Main Authors: | , , , , , , , , , , , , |
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container_end_page | 234 |
container_issue | 2 |
container_start_page | 227 |
container_title | Pure and applied chemistry |
container_volume | 81 |
creator | Cai, Qian Zhang, Hui Zou, Benli Xie, Xiaoan Zhu, Wei He, Gang Wang, Jing Pan, Xianhua Chen, Yu Yuan, Qiliang Liu, Feng Lu, Biao Ma, Dawei |
description | Ullmann-type coupling reactions between aryl halides and N-containing reagents, phenols, and other related nucleophilic agents are very valuable transformations for organic synthesis. Their conventional reaction conditions require high reaction temperatures. We describe here that some amino acids, either as substrates or ligands, can lead Cu-catalyzed C-N, C-O, C-S, and C-C bond formations work at relatively low temperatures. An
-substitution effect caused by NHCOR groups is discussed. Applications of these newly developed reactions to heterocycle preparation and asymmetric synthesis are also presented. |
doi_str_mv | 10.1351/PAC-CON-08-08-19 |
format | article |
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-substitution effect caused by NHCOR groups is discussed. Applications of these newly developed reactions to heterocycle preparation and asymmetric synthesis are also presented.</description><subject>Amino acids</subject><subject>Aromatic compounds</subject><subject>catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>copper</subject><subject>Coupling</subject><subject>Halides</subject><subject>Phenols</subject><subject>Reagents</subject><subject>Substitution reactions</subject><subject>Substrates</subject><subject>synthesis</subject><issn>0033-4545</issn><issn>1365-3075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp1UE1LxDAQDaLg-nH3GPAczUfTphdhKX7B4npwzyFN0zVLm9SkRfrvzVLBk_Bghpn33jAPgBuC7wjj5P59XaFq-4awOIKUJ2BFWM4RwwU_BSuMGUMZz_g5uIjxgDHOyoyugFz31nmotG3QEHzvR9PAXdf1yjk0zoOB2k9DZ90eBqP0aL2LULkGjp_GBqiGtNNqGVsHfdgrZzWMs0uEaOMVOGtVF831b70Eu6fHj-oFbbbPr9V6gzTLxYiaVnDe6Fo0bcGoUUrxMhNG81blBdWEc4FJIXiOa1FiohUXtaFZ3ZSk5cxwdgluF9_0xNdk4igPfgounZSUMkxyxmiWWHhh6eBjDKaVQ7C9CrMkWB5jlClGmWKUWBxByiR5WCTfqhtNaMw-THNq_vz_kwpCKS3YD4VTe6Q</recordid><startdate>20090101</startdate><enddate>20090101</enddate><creator>Cai, Qian</creator><creator>Zhang, Hui</creator><creator>Zou, Benli</creator><creator>Xie, Xiaoan</creator><creator>Zhu, Wei</creator><creator>He, Gang</creator><creator>Wang, Jing</creator><creator>Pan, Xianhua</creator><creator>Chen, Yu</creator><creator>Yuan, Qiliang</creator><creator>Liu, Feng</creator><creator>Lu, Biao</creator><creator>Ma, Dawei</creator><general>De Gruyter</general><general>Walter de Gruyter GmbH</general><scope>AAYXX</scope><scope>CITATION</scope><scope>K9.</scope></search><sort><creationdate>20090101</creationdate><title>Amino acid-promoted Ullmann-type coupling reactions and their applications in organic synthesis</title><author>Cai, Qian ; Zhang, Hui ; Zou, Benli ; Xie, Xiaoan ; Zhu, Wei ; He, Gang ; Wang, Jing ; Pan, Xianhua ; Chen, Yu ; Yuan, Qiliang ; Liu, Feng ; Lu, Biao ; Ma, Dawei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-df855dcb8df732eaaa5948ec5fa672c15580178560b8901ca58be24bd91f53e53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Amino acids</topic><topic>Aromatic compounds</topic><topic>catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>copper</topic><topic>Coupling</topic><topic>Halides</topic><topic>Phenols</topic><topic>Reagents</topic><topic>Substitution reactions</topic><topic>Substrates</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cai, Qian</creatorcontrib><creatorcontrib>Zhang, Hui</creatorcontrib><creatorcontrib>Zou, Benli</creatorcontrib><creatorcontrib>Xie, Xiaoan</creatorcontrib><creatorcontrib>Zhu, Wei</creatorcontrib><creatorcontrib>He, Gang</creatorcontrib><creatorcontrib>Wang, Jing</creatorcontrib><creatorcontrib>Pan, Xianhua</creatorcontrib><creatorcontrib>Chen, Yu</creatorcontrib><creatorcontrib>Yuan, Qiliang</creatorcontrib><creatorcontrib>Liu, Feng</creatorcontrib><creatorcontrib>Lu, Biao</creatorcontrib><creatorcontrib>Ma, Dawei</creatorcontrib><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><jtitle>Pure and applied chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cai, Qian</au><au>Zhang, Hui</au><au>Zou, Benli</au><au>Xie, Xiaoan</au><au>Zhu, Wei</au><au>He, Gang</au><au>Wang, Jing</au><au>Pan, Xianhua</au><au>Chen, Yu</au><au>Yuan, Qiliang</au><au>Liu, Feng</au><au>Lu, Biao</au><au>Ma, Dawei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Amino acid-promoted Ullmann-type coupling reactions and their applications in organic synthesis</atitle><jtitle>Pure and applied chemistry</jtitle><date>2009-01-01</date><risdate>2009</risdate><volume>81</volume><issue>2</issue><spage>227</spage><epage>234</epage><pages>227-234</pages><issn>0033-4545</issn><eissn>1365-3075</eissn><abstract>Ullmann-type coupling reactions between aryl halides and N-containing reagents, phenols, and other related nucleophilic agents are very valuable transformations for organic synthesis. Their conventional reaction conditions require high reaction temperatures. We describe here that some amino acids, either as substrates or ligands, can lead Cu-catalyzed C-N, C-O, C-S, and C-C bond formations work at relatively low temperatures. An
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language | eng |
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source | Free Full-Text Journals in Chemistry |
subjects | Amino acids Aromatic compounds catalysis Chemical reactions Chemical synthesis copper Coupling Halides Phenols Reagents Substitution reactions Substrates synthesis |
title | Amino acid-promoted Ullmann-type coupling reactions and their applications in organic synthesis |
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