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Selective Synthesis of Cyclic Nitroene‐Sulfonamides from Aliphatic Sulfamides and NOBF4

Von Wiley-VCH zur Verfügung gestellt

An efficient regio- and site-selective desaturation and β-nitration of cyclic aliphatic amides through a selective HAT/oxidative desaturation/electrophilic nitration process was realized.


Abstract

Described herein is the development of a desaturation and N-β-nitration reaction of cyclic amides, which is achieved by a selective hydrogen atom transfer (HAT)/oxidative desaturation/electrophilic nitration process. In this procedure, di-tert-butyl peroxide (DTBP) acted both as the oxidant and HAT reagent, and electrophilic NOBF4 as nitration source. Notably, the application of produced cyclic nitroene-sulfonamides was showcased by their efficient transformations into 3-piperidones and poly-substituted piperidine derivatives.

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