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Radical-Hydroboration-Involved One-Pot Synthesis of Boron-Handled Glycol Derivatives
Synlett ( IF 1.7 ) Pub Date : 2020-06-16 , DOI: 10.1055/s-0040-1707142
Feng-Lian Zhang , Yi-Feng Wang , Bi-Yang Zhuang , Ji-Kang Jin

A one-pot two-step protocol for the direct synthesis of boron-handled glycol derivatives is reported. The procedure starts by an NHC–boryl-radical-promoted regioselective hydroboration of glycol-protected cinnamaldehydes. After that, the reaction mixture is treated with pinacol in the presence of HCl, leading to the direct formation of pinacol boronate handled glycol monoalkyl ethers. In this acid-triggered conversion, a reductive ring-opening of glycol-derived acetal moiety takes place, during which an NHC–borane unit serves as the hydride source.

中文翻译:

硼处理乙二醇衍生物的自由基加氢反应一锅法合成

报告了直接合成硼处理的乙二醇衍生物的一锅两步协议。该过程从乙二醇保护的肉桂醛的 NHC-硼基自由基促进的区域选择性硼氢化反应开始。之后,反应混合物在 HCl 存在下用频哪醇处理,导致直接形成频哪醇硼酸酯处理的二醇单烷基醚。在这种酸引发的转化中,乙二醇衍生的缩醛部分发生还原性开环,在此期间 NHC-硼烷单元作为氢化物源。
更新日期:2020-06-16
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