Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 13, Pages 5153-5159Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034064e
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- NIGMS NIH HHS [R01 GM63167] Funding Source: Medline
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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 3 with 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.
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