Catalytic Silane‐Reduction of Carboxylic Esters and Lactones: Selective Synthetic Methods to Aldehydes, Lactols, and Ethers via Silyl Acetal Intermediates,ChemistrySelect

当前位置： X-MOL 学术 › ChemistrySelect › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Catalytic Silane‐Reduction of Carboxylic Esters and Lactones: Selective Synthetic Methods to Aldehydes, Lactols, and Ethers via Silyl Acetal Intermediates
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-03-15 , DOI: 10.1002/slct.201703033
Satomi Hosokawa ₁ , Motoki Toya ₁ , Ariki Noda ₁ , Masato Morita ₁ , Takaki Ogawa ₁ , Yukihiro Motoyama ₁

Affiliation

Practical procedures for the production of aldehydes, lactols, and ethers are offered by the palladium‐catalyzed silane‐reduction of carboxylic esters and lactones. The partial reduction of carboxylic esters or lactones with 1,1,3,3‐tetramethyldisiloxane in the presence of commercially available palladium on carbon (Pd/C) and some copper compounds as a co‐catalyst smoothly proceeds under mild conditions to afford the silyl acetal derivatives in high yields, which are easily converted to the corresponding aldehydes or lactols by hydrolysis of silyloxy group. On the other hand, deoxygenated ethers are obtained with high selectivity by treatment of silyl acetals with catalytic amounts of Me₃SiOTf at –78 °C or stoichiometric amounts of BF₃•OEt₂ at ambient temperature.

中文翻译：

羧酸酯和内酯的催化硅烷还原：通过甲硅烷基缩醛中间体合成醛，丙二醇和醚的选择性合成方法

钯催化的羧酸酯和内酯的硅烷还原提供了生产醛，丙二醇和醚的实用程序。在市售的钯碳（Pd / C）和一些铜化合物作为助催化剂的存在下，用1,1,3,3-四甲基二硅氧烷部分还原羧酸酯或内酯，在温和条件下平稳进行，得到甲硅烷基乙缩醛衍生物，收率高，可通过甲硅烷氧基的水解容易地转化为相应的醛或乳醇。另一方面，通过在–78°C下用催化量的Me ₃ SiOTf或化学计量的BF ₃ •OEt ₂处理甲硅烷基乙缩醛，可以高选择性地获得脱氧醚。在环境温度下。

更新日期：2018-03-15

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11