Catalytic hydroboration of aldehydes and ketones with sodium hydride: Application to chemoselective reduction of aldehydes over ketones

  • Shin, Won Kyu
  • Kim, Hanbi
  • Jaladi, Ashok Kumar
  • An, Duk Keun
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33
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33

초록

Sodium hydride-promoted catalytic hydroboration of aldehydes and ketones with pinacolborane (HBpin) was examined, and 10 mol% of NaH was found to cause the HBpin to participate in hydroboration in a convenient and efficient manner at mild reaction conditions. Further chemoselective hydroboration of aldehyde over ketone functionality was also analyzed. In addition, no hydroboration was observed form ester, acyl chloride, amide, nitrile, alkene, alkyne, alkyl halide and epoxide functional groups indicate that present system (HBpin, NaH) is highly selective for aldehydes and ketones. (C) 2018 Elsevier Ltd. All rights reserved.

키워드

Catalytic hydroborationAldehydes and ketonesSodium hydridePinacolborane (HBpin)ChemoselectiveCROSS-COUPLING REACTIONSCARBONYL-COMPOUNDSSELECTIVE HYDROBORATIONEFFICIENT HYDROBORATIONCOMPLEXESHYDROGENATIONPINACOLBORANEORGANOBORANESDIOXIDEALKENES
제목
Catalytic hydroboration of aldehydes and ketones with sodium hydride: Application to chemoselective reduction of aldehydes over ketones
저자
Shin, Won KyuKim, HanbiJaladi, Ashok KumarAn, Duk Keun
DOI
10.1016/j.tet.2018.09.031
발행일
2018-10-25
유형
Article
저널명
Tetrahedron
74
43
페이지
6310 ~ 6315