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

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 react...

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Bibliographic Details
Published inSynlett no. 20; pp. 3039 - 3044
Main Authors Zhichkin, Paul E., Krasutsky, Sergiy G., Krishnamoorthy, Ravi
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
regioselectivity
REAGENTS
ACIDS
REACTIVITY
metalation
FUNCTIONALIZATION
ARYLMAGNESIUM
formamidine
protecting groups
SUBSTITUTED ANILINES
LITHIATION
DERIVATIVES
ELABORATION
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Summary: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.
ISSN:0936-5214
DOI:10.1055/s-0030-1259058