4.7 Article

Samarium(iii) catalyzed synthesis of alkenylboron compounds via hydroboration of alkynes

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 14, Pages 3802-3808

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00513h

Keywords

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Funding

  1. National Natural Science Foundation of China [21572162]
  2. Foundation of Wenzhou Basic Scientific Research Project [G20190009]
  3. Xinmiao Foundation of Zhejiang Province [2020R434057]

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The homoleptic lanthanide complex Sm[N(TMS)(2)](3) is an efficient rare-earth catalyst for the hydroboration of alkynes, as demonstrated through gram-scale synthesis and subsequent transformations. The reaction mechanism was elucidated through isotopic labeling experiments, H-1 NMR monitoring, and kinetic studies.
The homoleptic lanthanide complex Sm[N(TMS)(2)](3) is an efficient rare-earth catalyst for the hydroboration of alkynes to the corresponding alkenylboron compounds. Practical applications were demonstrated through a gram-scale synthesis and further transformations of an alkenylboron ester to a series of functional compounds. Isotopic labeling experiments, H-1 NMR monitoring and kinetic studies were conducted to elucidate the reaction mechanism.

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