Fig. 2: Reactivity evaluation of umpolung N-cyanation reaction. | Nature Communications

Fig. 2: Reactivity evaluation of umpolung N-cyanation reaction.

From: Reverse polarity of amide nitrogen enables expedient access to N-cyano amides

Fig. 2

A Variation of substituents on the carbonyl group in O-tosyl hydroxamates. B Variation of N-substitution in O-tosyl hydroxamates nitrogen. C Chemoselective N-cyanation. D Unsuccessful substrates. Reaction conditions: O-tosyl hydroxamate (0.1 mmol, 1.0 equiv.), TMSCN (1.5 equiv.) and CsF (2.0 equiv.) in MeCN (0.05 M), air, 0 °C, 8–20 h. aTMSCN (2.5 equiv.) and CsF (3.0 equiv.) were used in MeCN (0.05 M), air, 50 °C, 2–7 h. b0.3 mmol scale. c2.0 equiv. of 18-crown-6 was used. brsm based on recovered starting material.

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