The Journal of organic chemistry

Tandem intramolecular silylformylation and silicon-assisted cross-coupling reactions. Synthesis of geometrically defined α, β-unsaturated aldehydes

SE Denmark, T Kobayashi

Index: Denmark, Scott E.; Kobayashi, Tetsuya Journal of Organic Chemistry, 2003 , vol. 68, # 13 p. 5153 - 5159

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Citation Number: 60

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 3 with various aryl iodides 7 in the presence of [(allyl) PdCl] 2, CuI, a hydrosilane, and KF⊙ 2H2O in DMF at room temperature provided the α, β-unsaturated aldehyde ...

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