Metal-free synthesis of secondary amides using N-Boc-O-tosylhydroxylamine as nitrogen source via Beckmann rearrangement. (25th July 2022)

• Record Type: Journal Article
• Authors: Jat, Jawahar L.; Kumar, Puneet; Verma, Saumya; Chandra, Dinesh; Singh, Vikram; Tiwari, Bhoopendra
• Is Part Of: New journal of chemistry. Volume 46:Number 31(2022)
• Page Start: 14782
• Page End: 14785
• Publication Date: 2022-07-25
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj02755k
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : An efficient methodology for the direct synthesis of secondary amides from ketones has been developed by using N -Boc- O -tosylhydroxylamine (TsONHBoc). Abstract : Herein, we report the first direct method for the synthesis of secondary amides from ketones via the Beckmann rearrangement using N -Boc- O -tosylhydroxylamine (TsONHBoc) as the aminating agent. This reagent is expected to play a dual role, first in the formation of the activated oxime intermediate, and then via facilitation of the amide formation as a Brønsted acid by the tosylic acid by-product. The metal and additive-free one-step method progresses in TFE solvent through the in situ generation of the primary amine reagent (TsONH2 ), and produces a water-soluble by-product.