Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation
Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation
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DOI：
10.1002/anie.201603424
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发表时间：
2016-07-11
影响因子：
16.6
通讯作者：
Grubbs, Robert H.
中科院分区：
文献类型：
--
作者：
Chu, Crystal K.;Ziegler, Daniel T.;Grubbs, Robert H.
烯丙基氟化物的选择性Wacker氧化反应在亚硝酸盐催化剂作用下进行。该方法代表了制备β-氟化醛的直接途径。具有多种官能团的烯丙基氟以高产率和非常高的区域选择性转化。此外，未纯化的醛产物用作多用途中间体，因此能够获得各种氟化结构单元。初步的机理研究表明，诱导效应对氧化的速率和区域选择性有很大的影响。
An aldehyde-selective Wacker-type oxidation of allylic fluorides proceeds with a nitrite catalyst. The method represents a direct route to prepare beta-fluorinated aldehydes. Allylic fluorides bearing a variety of functional groups are transformed in high yield and very high regioselectivity. Additionally, the unpurified aldehyde products serve as versatile intermediates, thus enabling access to a diverse array of fluorinated building blocks. Preliminary mechanistic investigations suggest that inductive effects have a strong influence on the rate and regioselectivity of the oxidation.