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Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition.

  • Barzanò G Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.
  • Cheseaux A Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.
  • Hu X Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering , Ecole Polytechnique Fédérale de Lausanne (EPFL) , ISIC-LSCI, BCH 3305, Lausanne 1015 , Switzerland.
  • 2019-01-10
Published in:
  • Organic letters. - 2019
Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry
English Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides. The Z-vinyl boronate products are easily converted to other Z-alkenes by transformation of the boronate group. The method is applied for the formal total synthesis of a 5-HT2c receptor agonist.
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  • English
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green
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https://sonar.ch/global/documents/282408
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