期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 68, 期 13, 页码 5153-5159出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo034064e
关键词
-
资金
- NIGMS NIH HHS [R01 GM63167] Funding Source: Medline
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.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据