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Palladium(0)-catalyzed suzuki-miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides.
J Org Chem. 2006 Jul 21; 71(15):5743-7.JO

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 < or =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.

Authors+Show Affiliations

Molander GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Fumagalli T
No affiliation info available

MeSH

AlkenesBoratesBromidesCatalysisHeterocyclic CompoundsHydrocarbons, HalogenatedMolecular StructurePalladiumPotassiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16839157

Citation

Molander, Gary A., and Tiziano Fumagalli. "Palladium(0)-catalyzed Suzuki-miyaura Cross-coupling Reactions of Potassium Aryl- and Heteroaryltrifluoroborates With Alkenyl Bromides." The Journal of Organic Chemistry, vol. 71, no. 15, 2006, pp. 5743-7.
Molander GA, Fumagalli T. Palladium(0)-catalyzed suzuki-miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides. J Org Chem. 2006;71(15):5743-7.
Molander, G. A., & Fumagalli, T. (2006). Palladium(0)-catalyzed suzuki-miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides. The Journal of Organic Chemistry, 71(15), 5743-7.
Molander GA, Fumagalli T. Palladium(0)-catalyzed Suzuki-miyaura Cross-coupling Reactions of Potassium Aryl- and Heteroaryltrifluoroborates With Alkenyl Bromides. J Org Chem. 2006 Jul 21;71(15):5743-7. PubMed PMID: 16839157.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(0)-catalyzed suzuki-miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates with alkenyl bromides. AU - Molander,Gary A, AU - Fumagalli,Tiziano, PY - 2006/7/15/pubmed PY - 2007/6/15/medline PY - 2006/7/15/entrez SP - 5743 EP - 7 JF - The Journal of organic chemistry JO - J Org Chem VL - 71 IS - 15 N2 - 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 < or =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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16839157/Palladium_0__catalyzed_suzuki_miyaura_cross_coupling_reactions_of_potassium_aryl__and_heteroaryltrifluoroborates_with_alkenyl_bromides_ L2 - https://doi.org/10.1021/jo0608366 DB - PRIME DP - Unbound Medicine ER -