Ex-situ generation of gaseous nitriles in two-chamber glassware for facile haloacetimidate synthesis

• Nikolai B. Akselvoll,
• Jonas T. Larsen and
• Christian M. Pedersen

Beilstein J. Org. Chem. 2025, 21, 2465–2469, doi:10.3762/bjoc.21.188

• donor; haloacetimidates; haloacetonitrile; two-chamber reactor; Introduction Trifluoroacetonitrile is an electrophilic reagent that has seen a variety of uses, mostly for incorporating trifluoromethyl groups into organic compounds [1]. As an example it has been successfully utilized for the synthesis

• of trifluoroacetonitrile and our set-up using a two-chamber reactor. Glycosyl haloacetimidates synthesized using the two-chamber method. Synthesis of arylmethylene fluoroacetimidates using the two-chamber method. Reactions in chambers A and B. Chamber A: generation of the haloacetonitrile by

• dehydration of the corresponding haloacetamide. Chamber B: reaction between the generated haloacetonitrile and an O-nucleophile resulting in a haloacetimidate. Supporting Information Supporting Information File 4: Experimental section.