Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 20, Issue 11, Pages 1967-1973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.6b00292
Keywords
anilines; diazotization; triazoles; click chemistry; dipolar cycloaddition; flow
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Funding
- NSERC (Canada)
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The conversion of commercially available anilines into triazole products was realized using a telescoped three-reactor flow diazotization, azidodediazotization, and [3 + 2] dipolar cycloaddition process. The diazotization azidodediazotization sequence was accelerated by means of an ultrasonic bath resulting in a degassed, segmented effluent. An automated continuous flow unit controlled by custom software created in-house was used to collect the aryl azide stream and restore it to a continuous column of the reagent. When combined with a variety of dipolarophiles, 1-aryl-[1,2,3]-triazoles were thus assembled by either copper catalyzed alkyne azide cycloaddition (CuAAC) or Huisgen cycloaddition reactions.
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