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Photocatalytic Carbosulfonylation/Cyclization of N -Homoallyl and N -Allyl Aldehyde Hydrazones toward Sulfonylated Tetrahydropyridazines and Dihydropyrazoles.

Yechun WuXian WuLingli LiuJin-Tao YuChangduo Pan
Published in: Organic letters (2023)
N '-Benzylidene- N -homoallylacetohydrazides were designed and synthesized as novel skeletons for the construction of functionalized tetrahydropyridazines. A series of aryl- and alkylsulfonylated tetrahydropyridazines were obtained in yields of up to 94% employing sulfonyl chlorides as the sulfonyl radical sources under visible-light irradiation. Besides, sulfonylated dihydropyrazoles were also produced from N -allyl- N '-benzylideneacetohydrazides. Mechanistic investigations indicated that both energy transfer and single electron transfer processes were involved in accomplishing the radical 6/5- endo - trig cyclization to the C═N bond.
Keyphrases
  • visible light
  • electron transfer
  • energy transfer
  • quantum dots
  • drinking water
  • radiation induced
  • molecularly imprinted
  • gold nanoparticles
  • liquid chromatography