Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Potassium Aryl- and Heteroaryltrifluoroborates
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- 1 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (11) , 4302-4314
- https://doi.org/10.1021/jo0342368
Abstract
An extended study of the reactivity of potassium aryl- and heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5−2%) of PdCl2(dppf)·CH2Cl2 efficiently catalyzes the reactions. Under either condition, reactions can generally be carried out in an open atmosphere.Keywords
This publication has 31 references indexed in Scilit:
- Pd/C as a Reusable Catalyst for the Coupling Reaction of Halophenols and Arylboronic Acids in Aqueous MediaThe Journal of Organic Chemistry, 2002
- Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous PalladiumOrganic Letters, 2001
- Suzuki coupling with ligandless palladium and potassium fluorideChemical Communications, 2001
- New Efficient Nickel- and Palladium-Catalyzed Cross-Coupling Reactions Mediated by Tetrabutylammonium IodideOrganic Letters, 1999
- Solventless Suzuki Coupling Reactions on Palladium-Doped KF/Al2O3Organic Letters, 1999
- Ni(II)-Catalyzed Cross-Coupling between Polyfunctional Arylzinc Derivatives and Primary Alkyl IodidesJournal of the American Chemical Society, 1998
- Metal‐Catalyzed Cross‐Coupling ReactionsPublished by Wiley ,1998
- Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladiumTetrahedron Letters, 1996
- High yields of unsymmetrical biaryls via cross coupling of arylboronic acids with haloarenes using a modified Suzuki-Beletskaya procedureJournal of the Chemical Society, Chemical Communications, 1994
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie International Edition in English, 1986