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Suzuki−Miyaura Cross-Coupling of Potassium Trifluoroboratohomoenolates
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Abstract
Ketone-, ester-, and amide-containing potassium trifluoroboratohomoenolates were prepared in good to excellent yields from the corresponding unsaturated carbonyl compounds. They were shown to be effective coupling partners in the Suzuki-Miyaura reaction with a variety of electrophiles including electron-rich and electron-poor aryl bromides and -chlorides.
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).
Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane
Gary A. Molander and Silas A. McKeeOrganic Letters2011 Article ASAPCopper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane
Gary A. Molander and Silas A. McKeeOrganic Letters2011 Article ASAPThe copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane has been developed. This diboron reagent allows direct, efficient access to boronic acids and their derivatives. Primary, secondary, and tertiary α,β-...
Chemoselective Suzuki Coupling of Diborylmethane for Facile Synthesis of Benzylboronates
Kohei Endo, Takahiro Ohkubo, and Takanori ShibataOrganic Letters2011 Article ASAPChemoselective Suzuki Coupling of Diborylmethane for Facile Synthesis of Benzylboronates
Kohei Endo, Takahiro Ohkubo, and Takanori ShibataOrganic Letters2011 Article ASAPThe chemoselective Pd-catalyzed Suzuki–Miyaura cross-coupling reaction using a diborylmethane is reported. The use of an equimolar amount of base with a diborylmethane realized chemoselective coupling for the synthesis of various benzylboronate ...
Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492
Stereospecific Cross-Coupling of Secondary Alkyl β-Trifluoroboratoamides
Deidre L. Sandrock, Ludivine Jean-Gérard, Cheng-yi Chen, Spencer D. Dreher, and Gary A. MolanderJournal of the American Chemical Society2010 132 (48), 17108-17110Stereospecific Cross-Coupling of Secondary Alkyl β-Trifluoroboratoamides
Deidre L. Sandrock, Ludivine Jean-Gérard, Cheng-yi Chen, Spencer D. Dreher, and Gary A. MolanderJournal of the American Chemical Society2010 132 (48), 17108-17110The stereospecific cross-coupling of enantioenriched nonbenzylic secondary alkyl boron compounds has been achieved. The high selectivity toward product formation over an undesired β-H elimination pathway is achieved via an intramolecular coordination of ...
Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium β-Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides
Gary A. Molander, Inji Shin, and Ludivine Jean-GérardOrganic Letters2010 12 (19), 4384-4387Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions of Enantiomerically Enriched Potassium β-Trifluoroboratoamides with Various Aryl- and Hetaryl Chlorides
Gary A. Molander, Inji Shin, and Ludivine Jean-GérardOrganic Letters2010 12 (19), 4384-4387Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki−Miyaura cross-coupling reactions were carried ...
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History
- Published In Issue May 01, 2008
- Article ASAPApril 08, 2008
- Received: February 16, 2008
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