4.8 Article

Aryl Boronic Esters Are Stable on Silica Gel and Reactive under Suzuki-Miyaura Coupling Conditions

Journal

ORGANIC LETTERS
Volume 24, Issue 19, Pages 3510-3514

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01174

Keywords

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Funding

  1. JSPS KAKENHI [16K08164, 19K06996, 18KK0154]
  2. Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED [JP21am0101084, 22ama121054]
  3. Research Foundation for Pharmaceutical Sciences, Hoanshya
  4. Takeda Science Foundation
  5. Sasakawa Scientific Research Grant
  6. Koshiyama Science and Technology Promotion Foundation
  7. Nagai Memorial Research Scholarship
  8. Grants-in-Aid for Scientific Research [16K08164, 18KK0154, 19K06996] Funding Source: KAKEN

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A wide range of aryl boronic esters were synthesized and easily purified, showing higher yields in Suzuki-Miyaura couplings compared to aryl boronic acids or pinacol esters.
A wide range of aryl boronic 1,1,2,2-tetraethylethylene glycol esters [ArB(Epin)s] were readily synthesized. Purifying aryl boronic esters by conventional silica gel chromatography is generally challenging; however, these introduced derivatives are easily purified on silica gel and isolated in excellent yields. We subjected the purified ArB(Epin) to Suzuki-Miyaura couplings, which provided higher yields of the desired biaryl products than those obtained using the corresponding aryl boronic acids or pinacol esters.

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