Fluorous triphasic reactions: Transportative deprotection of fluorous silyl ethers with concomitant purification
Fluorous triphasic reactions: Transportative deprotection of fluorous silyl ethers with concomitant purification
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DOI：
10.1021/ja011716c
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发表时间：
2001-10-17
影响因子：
15
通讯作者：
Curran, DP
中科院分区：
文献类型：
--
作者：
Nakamura, H;Linclau, B;Curran, DP
在典型的有机反应中使用不纯的起始材料通常是生产不纯产物的配方。因此，每个有机反应之后通常进行分离。尽管有效率优势，但反应和分离很少以任何实质性的方式耦合。2在此，我们描述了“氟三相反应”的第一个例子。在这些工艺中，液-液分离直接与化学反应相结合，以从不纯的前体开始提供纯产品。反应和分离是同时发生的，而不是顺序发生的，反应驱动分离。氟三相反应源自氟两相反应3和其他基于氟/有机液液萃取的技术。4他们还扩展了所谓的“氟合成”技术，其中有机分子在合成的一部分过程中可逆地用氟标记物标记。这些技术通常依赖于固-液萃取，因为液-液萃取所需的氟的数量过大。[6]三个液相（通常两个水相，一个有机相）的传输特性是众所周知的，[7]但很少用于合成。
The use of an impure starting material in a typical organic reaction is generally a recipe for producing an impure product. Accordingly, each organic reaction is usually followed by a separation. Despite the efficiency advantage, reactions and separations are rarely coupled in any substantive way. 2 Herein, we describe the first examples of “fluorous triphasic reactions”. In these processes, a liquid-liquid separation is directly coupled with a chemical reaction to provide a pure product starting from an impure precursor. The reaction and separation occur simultaneously rather than sequentially, and the reaction drives the separation.Fluorous triphasic reactions emanate from fluorous biphasic reactions3 and other techniques based on fluorous/organic liquidliquid extractions. 4 They also extend so-called “fluorous synthesis” techniques in which organic molecules are reversibly tagged with fluorous tags during a part of the synthesis. 5 These techniques typically rely on solid-liquid extraction because the number of fluorines needed for liquid-liquid extractions is unduly large. 6 The transportation features of three liquid phases (usually two aqueous, one organic) are well-known7 but are rarely used in synthesis.