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N,N-Diisopropylformamidine (DIFA) Protection of Anilines in Metalation Reactions

  作者 ZHICHKIN PAUL E; KRASUTSKY SERGIY G; KRISHNAMOORTHY RAVI  
  选自 期刊  SYNLETT;  卷期  2010年-20;  页码  3039-3044  
  关联知识点  
 

[摘要]A novel N,N-diisopropylformamidine (DIFA) protecting group for anilines was studied. Metalation is often metal-directed by this weakly coordinating and bulky group, making it complementary to ortho-metalation directed by tert-butylcarbamate and pivaloylamide groups and to regular electrophilic reactions of anilines. Importantly, DIFA is removed under nucleophilic conditions and is stable toward acids, thus being orthogonal to tert-butylcarbamate, N-tert-butylamide, and other acid-labile protecting groups.

 
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