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Bronsted Acid Catalyzed Friedel-Crafts Alkylation Reactions of Trifluoromethyl-alpha,beta-ynones with Indoles

  作者 SASAKI SHIGERU; IKEKAME YUTA; TANAYAMA MANABU; YAMAUCHI TAKAYASU; HIGASHIYAMA KIMIO  
  选自 期刊  SYNLETT;  卷期  2012年-18;  页码  2699-2703  
  关联知识点  
 

[摘要]The successful development of a Bronsted acid catalyzed Friedel-Crafts alkylation reaction between trifluoromethyl-alpha,beta-ynones and indoles has been described. The reaction is catalyzed by benzoic acid (5 mol%), with the indoles adding to the carbonyl carbon of the trifluoromethyl-alpha,beta-ynones producing the corresponding 1,2-addition products as trifluoromethyl propargyl alcohols in high yields. Furthermore, treatment of the product with indoles in the presence of trifluoroacetic acid (10 mol%) afforded trifluoromethyl-functionalized unsymmetrical bis(indolyl)propynes in high yields.

 
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