Triflic Anhydride Promoted Synthesis of Primary Amides and their Conversion into Nitriles

Abstract A facile, two-pot conversion of carboxylic acids into the corresponding nitriles has been developed using triflic anhydride as a promoter and aqueous NH 4 OH as a source of nitrogen. The methodology involves synthesis of primary amides from carboxylic acids as the key first step using trifl...

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Published inSynOpen (2017) Vol. 2; no. 2; pp. 0180 - 0191
Main Authors Rana, Anil, Kumar, Varun, Tiwari, Lata, Thakur, Anamika, Meena, Chhuttan Lal, Mahajan, Dinesh
Format Journal Article
LanguageEnglish
Published Stuttgart · New York Georg Thieme Verlag 01.04.2018
Georg Thieme Verlag KG
Subjects
ammonium ­hydroxide
nitriles
primary amides
triflic anhydride
nitriles
primary amides
triflic anhydride
ammonium ­hydroxide
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Summary:Abstract A facile, two-pot conversion of carboxylic acids into the corresponding nitriles has been developed using triflic anhydride as a promoter and aqueous NH 4 OH as a source of nitrogen. The methodology involves synthesis of primary amides from carboxylic acids as the key first step using triflic anhydride and aqueous NH 4 OH as a source of ­nitrogen. Triflic anhydride is also found to be an excellent reagent for conversion of primary amides into nitriles, affording high yields with considerable chemoselectivity and functional group tolerance. In spite of the mild reaction conditions and broad substrate scope for the two-step conversions, all attempts for one-pot domino conversion of acids into nitriles exhibited limited success because of poor yields.
ISSN:2509-9396
2509-9396
DOI:10.1055/s-0037-1610154