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• W2949785881 abstract "The palladium- and copper-catalyzed cross-coupling reactions of cyclic silyl ethers with aryl iodides are reported. Silyl ethers 3 were readily prepared by intramolecular silylformylation of homopropargyl silyl ethers 2 under a carbon monoxide atmosphere. The reaction of cyclic silyl ethers 3with various aryl iodides 7 in the presence of [(allyl)PdCl](2), CuI, a hydrosilane, and KF.2H(2)O in DMF at room temperature provided the alpha,beta-unsaturated aldehyde coupling products 8 in high yields. The need for copper in this process suggested that transmetalation from silicon to copper is an important step in the mechanism. Although siloxane 3 and the product 8 are not stable under basic conditions, KF.2H(2)O provided the appropriate balance of reactivity toward silicon and reduced basicity. The addition of a hydrosilane to [(allyl)PdCl](2) was needed to reduce the palladium(II) to the active palladium(0) form." @default.
• W2949785881 created "2019-06-27" @default.
• W2949785881 creator A5060673018 @default.
• W2949785881 creator A5086108389 @default.
• W2949785881 date "2003-06-01" @default.
• W2949785881 modified "2023-10-15" @default.
• W2949785881 title "Tandem Intramolecular Silylformylation and Silicon-Assisted Cross-Coupling Reactions. Synthesis of Geometrically Defined α,β-Unsaturated Aldehydes" @default.
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• W2949785881 doi "https://doi.org/10.1021/jo034064e" @default.
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