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CC BY-ND-NC 4.0 · SynOpen 2018; 02(02): 0180-0191
DOI: 10.1055/s-0037-1610154
DOI: 10.1055/s-0037-1610154
paper
Triflic Anhydride Promoted Synthesis of Primary Amides and their Conversion into Nitriles
We would like to thank the Translational Health Science and Technology Institute (THSTI) for intramural research funding and DBT-BIRAC for grant BT/CRS0200/CRS-10/16.Further Information
Publication History
Received: 24 March 2018
Accepted after revision: 30 April 2018
Publication Date:
08 June 2018 (online)
Abstract
A facile, two-pot conversion of carboxylic acids into the corresponding nitriles has been developed using triflic anhydride as a promoter and aqueous NH4OH 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 NH4OH 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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610154.
- Supporting Information
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