Borane evolution and its application to organic synthesis using the phase-vanishing method

Nene Soga, Tomo Yoshiki, Aoi Sato, Takuji Kawamoto, Ilhyong Ryu, Hiroshi Matsubara*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Although borane is a useful reagent, it is difficult to handle. In this study, borane was generated in situ from NaBH4 or nBu4NBH4 with several oxidants using a phase-vanishing (PV) method. The borane generated was directly reacted with alkenes, affording the desired alcohols in good yields after oxidation with H2O2 under basic conditions. The selective reduction of carboxylic acids with the evolved borane was examined. The organoboranes generated by the PV method successfully underwent Suzuki–Miyaura coupling. Using this PV system, reactions with borane can be carried out easily and safely in a common test tube.

Original languageEnglish
Article number152977
JournalTetrahedron Letters
Volume69
DOIs
StatePublished - 13 Apr 2021

Keywords

  • Borane
  • Fluorous solvent
  • Gaseous reagents
  • Hydroboration
  • Phase-vanishing method

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