Development of Hydroxysulfenylation and Hydroxyalkylation Reaction of Conjugated imines

DOI

Bibliographic Information

Other Title
  • 共役イミン類のヒドロキシスルフィド化および ヒドロキシアルキル化反応の開発

Description

Radical-mediated domino reactions involving aerobic hydroxylation of alpha-imino radical have been developed. we first studied hydroxysulfenylation of conjugated imines. Treatment of conjugated imine with Et3B and thiophenol in the presence of O2 gave corresponding beta-hydroxysulfides with high regioselectivity and good yield. The reaction would proceed through radical pathway involving regioselective addition of thiyl radical and the subsequent trapping of the resulting alpha-imino radical with O2, in which the imino group enhances the stability of the intermediate radical. Hydroxyalkylation of conjugated imines was next examined. As expected, the hydroxyalkylation reaction using Et3B as radical initiator and ethyl radical source proceeded effectively to give the hydroxyalkylated product in good yield. An N-borylenamine was found to be a key intermediate in the proposed aerobic hydroxylation mechanism.

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Details 詳細情報について

  • CRID
    1390001205635322496
  • NII Article ID
    130006997847
  • DOI
    10.14895/hannou.35.0.79.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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