Efficient Guanidine-Catalyzed Alkylation of Indoles with Fluoromethyl Ketones in the presence of Water
A simple and efficient guanidine-catalyzed methodology for the direct preparation of trifluoromethyl-indolyl-phenylethanols in the presence of water is reported. This synthetically viable class of compounds is obtained in excellent yields (up to 98%) through Friedel−Crafts-type alkylation of indoles...
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| Veröffentlicht in: | Organic letters 2009-05, Vol.11 (10), p.2093-2096 |
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| container_title | Organic letters |
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| creator | Bandini, Marco Sinisi, Riccardo |
| description | A simple and efficient guanidine-catalyzed methodology for the direct preparation of trifluoromethyl-indolyl-phenylethanols in the presence of water is reported. This synthetically viable class of compounds is obtained in excellent yields (up to 98%) through Friedel−Crafts-type alkylation of indoles with aromatic fluoromethyl ketones. Exceptional reaction scope of indoles and alkylating agents is described. |
| doi_str_mv | 10.1021/ol9005079 |
| format | Article |
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Lett</addtitle><description>A simple and efficient guanidine-catalyzed methodology for the direct preparation of trifluoromethyl-indolyl-phenylethanols in the presence of water is reported. This synthetically viable class of compounds is obtained in excellent yields (up to 98%) through Friedel−Crafts-type alkylation of indoles with aromatic fluoromethyl ketones. Exceptional reaction scope of indoles and alkylating agents is described.</description><subject>Alkylation</subject><subject>Catalysis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Guanidine - chemistry</subject><subject>Hydrocarbons, Fluorinated - chemistry</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Ketones - chemistry</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><subject>Water - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE9LAzEQxYMoVqsHv4DkouBhNdk_2c2xlLYWC14KHpfs7ixNzSY1ySLrpzelpV48zbyZ3zyYh9AdJc-UxPTFKE5IRnJ-hq5oFidRTrL4_NQzMkLXzm0JoWHCL9GI8oSlQVyhdta2spagPV70QstGaoimwgs1_ECDJ-pzUMJLo7Fp8VI3RoHD39Jv8Fz1xpoO_GZQ-A280WEjNfYbwDsLDnQN-6MP4cHeoItWKAe3xzpG6_lsPX2NVu-L5XSyikRCEx-lFY8rmvMKqpjUBLKKZTkUDERBk6bhQbC6SDkXrKhYQoqUMcJTECkVrKqTMXo82O6s-erB-bKTrgalhAbTu5LlMSkKRgL4dABra5yz0JY7Kzthh5KScp9peco0sPdH077qoPkjjyEG4OEAiNqVW9NbHV78x-gXRBN9lg</recordid><startdate>20090521</startdate><enddate>20090521</enddate><creator>Bandini, Marco</creator><creator>Sinisi, Riccardo</creator><general>American Chemical Society</general><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>20090521</creationdate><title>Efficient Guanidine-Catalyzed Alkylation of Indoles with Fluoromethyl Ketones in the presence of Water</title><author>Bandini, Marco ; Sinisi, Riccardo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-4b92b179beb20c0e5b657e86ea813dd957e6c8499a68b6308466094ea41a6bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkylation</topic><topic>Catalysis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Guanidine - chemistry</topic><topic>Hydrocarbons, Fluorinated - chemistry</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Ketones - chemistry</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bandini, Marco</creatorcontrib><creatorcontrib>Sinisi, Riccardo</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bandini, Marco</au><au>Sinisi, Riccardo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Guanidine-Catalyzed Alkylation of Indoles with Fluoromethyl Ketones in the presence of Water</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2009-05, Vol.11 (10), p.2093-2096 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkylation Catalysis Combinatorial Chemistry Techniques Guanidine - chemistry Hydrocarbons, Fluorinated - chemistry Indoles - chemical synthesis Indoles - chemistry Ketones - chemistry Molecular Structure Stereoisomerism Water - chemistry |
| title | Efficient Guanidine-Catalyzed Alkylation of Indoles with Fluoromethyl Ketones in the presence of Water |
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