Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed CC bond-forming reactions

  title={Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed CC bond-forming reactions},
  author={Robert A. Batey and Tan D. Quach and Minggui Shen and Avinash N. Thadani and David Smil and Sze-Wan Li and D. Bruce MacKay},
  journal={Pure and Applied Chemistry},
  pages={43 - 55}
Abstract The use of air- and water-stable organoboron compounds for CC bond-forming reactions are reported. These studies include the Lewis acid-promoted additions of boronic esters to N-acyliminium ions and allyl and crotyltrifluoroborate salts to aldehydes. Aryl and alkenyltrifluoroborate salts will add to aldehydes under the influence of rhodium catalysis or in the presence of zinc metal. These salts also participate in palladium-catalyzed SuzukiMiyaura and other cross-coupling reactions… 
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( a ) N . A . Petasis and I . Akritopoulou
  • Tetrahedron Lett .
  • 1999
K . Omoto and H . Fujimoto
  • J . Org . Chem .
  • J . Org . Chem .
  • 1994
, I . A . Zaviolov
  • J . Am . Chem . Soc .