三氟甲磺酸三氟甲酯的反应研究进展
An Overview of the Reactions with Trifluoromethyl Trifluoromethanesulfonate
Received date: 2022-02-12
Revised date: 2022-03-13
Online published: 2022-03-30
Supported by
Wuhan University of Technology
含氟化合物的合成离不开含氟试剂的开发和应用. 由于氟原子的特殊效应, 含氟试剂通常表现出不同于不含氟类似物的反应性质和规律. 在众多三氟甲氧基化试剂中, 三氟甲磺酸三氟甲酯因具有制备简单、成本低廉及反应性质多样等优点, 近年来受到越来越多的关注. 该试剂可以在氟负离子引发下快速分解得到三氟甲氧基阴离子, 因此它常被看作是三氟甲氧基阴离子的储存体, 被广泛用于亲核三氟甲氧基化反应. 另外, 三氟甲磺酸三氟甲酯在亲核试剂引发下分解产生的三氟甲氧基阴离子, 由于其热稳定性较差, 很容易进一步分解成氟光气和氟负离子, 因此它还可以被用作羰基化试剂、氟甲酰化试剂、缩合试剂和亲核氟化试剂. 重点介绍了三氟甲磺酸三氟甲酯在三氟甲氧基化反应、羰基化反应以及氟化反应中的研究进展.
冉龙玉 , 张成潘 . 三氟甲磺酸三氟甲酯的反应研究进展[J]. 有机化学, 2022 , 42(7) : 2045 -2054 . DOI: 10.6023/cjoc202202025
Synthesis of fluorine-containing compounds is greatly dependent upon the development and application of fluorinated reagents. Thanks to the unique fluorine effects, fluorinated reagents usually exhibit different properties and reaction profiles from those of the non-fluorinated analogues. Among various trifluoromethoxylation reagents, trifluoromethyl trifluoromethanesulfonate has drawn much attention in recent years because of its easy preparation, low cost and diverse reactivities. This reagent rapidly decomposes to form trifluoromethoxy anion in the presence of fluoride ion, thus regarded as a reservoir of trifluoromethoxy anion, and has been widely used in the nucleophilic trifluoromethoxylation reactions. Moreover, the trifluoromethoxy anion derived from trifluoromethyl trifluoromethanesulfonate and nucleophiles has poor thermal stability and tends to decompose at room temperature to afford fluorophosgene and fluorine anion, which can be used as a carbonylation reagent, a fluoroformylation reagent, a condensation agent or a nucleophilic fluorination reagent. The trifluoromethoxylation, carbonylation and fluorination reactions with trifluoromethyl trifluoromethanesulfonate as the reagent are reviewed.
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