Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Syntheses of Conjugated Dienes from 1-Alkenylboronic Acids by Palladium (II) Salt

  • Kim, Jin-Il (Department of Industrial Chemistry, Han Yang University) ;
  • Lee, Jong-Tae (Department of Industrial Chemistry, Han Yang University) ;
  • Yeo, Kyu-Dong (Department of Industrial Chemistry, Han Yang University)
  • Published : 1985.12.20
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Abstract

The reactions of (E)-1-hexenylboronic acid (1) or (E)-${\beta}$-phenylethenylboronic acid (2) with various olefins in acetonitrile at room temperature in the presence of lithium palladium chloride and triethylamine gave the corresponding (E, E)-conjugated dienes stereospecifically in good yields. (E)-${\beta}$-Phenylethenylboronic acid (2) was more reactive than (E)-1-hexenylboronic acid (1) in these vinylations. And these vinylations were also carried out catalytically when 10 mol % of lithium palladium chloride and cupric chloride, as the reoxidant of palladium, or 10 mol % of palladium acetate and mercuric acetate were added instead of stoichiometric amount of lithium palladium chloride.

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Cited by

  1. ChemInform Abstract: Syntheses of Conjugated Dienes from 1-Alkenylboronic Acids by Palladium(II) Salt. vol.17, pp.29, 1985, https://doi.org/10.1002/chin.198629115
  2. Catalyst-Controlled Regioselectivity in the Synthesis of Branched Conjugated Dienes via Aerobic Oxidative Heck Reactions vol.134, pp.40, 2012, https://doi.org/10.1021/ja307371w