Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with vinyl triflates β-substituted by a carbonyl group: efficient synthesis of β-boryl-α,β-unsaturated carbonyl compounds and their synthetic utility

• Ishiyama, Tatsuo

• Takagi, Jun

• Kamon, Akihiro

• Miyaura, Norio

Abstract

Cross-coupling reaction of bis(pinacolato)diboron with β-(trifluoromethanesulfonyloxy)-α,β-unsaturated carbonyl compounds was carried out in the presence of PdCl2(PPh3)2-2PPh3 (3 mol%) and KOPh in toluene or K2CO3 in dioxane for the synthesis of cyclic and acyclic β-boryl-α,β-unsaturated esters, amides, and ketones in high yields. The vinylboronates thus obtained readily participated in carbon-carbon bond formation, such as cross-coupling with vinyl triflates and 1,4-addition to α,β-unsaturated ketones.

Journal

• Journal of Organometallic Chemistry

  Journal of Organometallic Chemistry 687 (2), 284-290, 2003-12-07

  Elsevier

Keywords

• Bis(pinacolato)diboron
• Vinyl triflate
• Palladium catalyst
• Vinylboronate
• Cross-coupling

Details

• CRID: 1050282813993468032
• NII Article ID: 120005438249
• HANDLE: 2115/56318
• ISSN: 0022328X
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles