Palladium(0)-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Potassium Aryl- and Heteroaryltrifluoroborates with Alkenyl Bromides
- 24 June 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (15) , 5743-5747
- https://doi.org/10.1021/jo0608366
Abstract
Efficient palladium(0)-catalyzed Suzuki−Miyaura cross-couplings are described. The reactions involving potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides can generally be carried out using ≤2 mol % of palladium catalyst and 3 equiv of base in toluene/H2O. When stereodefined alkenyl bromides are employed, the resulting styrene derivatives are accessed stereospecifically. A variety of functional groups are tolerated in both coupling partners.Keywords
This publication has 17 references indexed in Scilit:
- Synthesis of the Side Chain Cross-Linked Tyrosine Oligomers Dityrosine, Trityrosine, and PulcherosineThe Journal of Organic Chemistry, 2005
- Total Synthesis of Serofendic Acids A and B Employing Tin-Free Homoallyl−Homoallyl Radical RearrangementOrganic Letters, 2005
- Suzuki−Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt SystemsOrganometallics, 2002
- Room-Temperature Alkyl−Alkyl Suzuki Cross-Coupling of Alkyl Bromides that Possess β HydrogensJournal of the American Chemical Society, 2001
- Suzuki coupling with ligandless palladium and potassium fluorideChemical Communications, 2001
- Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild ConditionsJournal of the American Chemical Society, 2000
- Highly Active Palladium Catalysts for Suzuki Coupling ReactionsJournal of the American Chemical Society, 1999
- Solventless Suzuki Coupling Reactions on Palladium-Doped KF/Al2O3Organic Letters, 1999
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986
- The study of α and β furanboronic acidsJournal of Heterocyclic Chemistry, 1975