三氟甲磺酸三氟甲酯的反应研究进展

doi:10.6023/cjoc202202025

摘要/Abstract

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.

关键词: 三氟甲磺酸三氟甲酯, 三氟甲氧基化, 羰基化, 氟化

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.

Key words: trifluoromethyl trifluoromethanesulfonate, trifluoromethoxylation, carbonylation, fluorination

引用此文

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.

Longyu Ran, Chengpan Zhang. An Overview of the Reactions with Trifluoromethyl Trifluoromethanesulfonate[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2045-2054.

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图/表 14

图式1. 三氟甲磺酸三氟甲酯的早期应用

Scheme 1. Initial application of trifluoromethyl trifluoromethanesulfonate

图式2. 三氟甲磺酸三氟甲酯在氟负离子引发下现场生成–OCF3阴离子

Scheme 2. In situ generation of –OCF3 anion from trifluoromethyl trifluoromethanesulfonate induced by fluoride ion

图式3. 三氟甲磺酸三氟甲酯的合成方法汇总

Scheme 3. A summary of synthetic methods for trifluoromethyl trifluoromethanesulfonate

图1. 目前已知的三氟甲氧基化试剂

Figure 1. Known trifluoromethoxylation reagents

图式4. CF3SO2OCF3在不同氟盐引发下对多种亲电试剂的三氟甲氧基化反应

Scheme 4. Trifluoromethoxylation of various electrophiles with CF3SO2OCF3 in the presence of different fluorides

图式5. 由CF3SO2OCF3衍生的[TAS][OCF3]在银盐促进下对芳基硼酸和芳基锡试剂的三氟甲氧基化反应

Scheme 5. Silver-mediated trifluoromethoxylation of arylboronic acids and aryltin compounds with [TAS][OCF3] derived from CF3SO2OCF3

图式6. 利用CF3SO2OCF3衍生的AgOCF3合成相对稳定的三氟甲氧基金属配合物

Scheme 6. Synthesis of the relatively stable trifluoromethoxy-metal complexes using AgOCF3 derived from CF3SO2OCF3

图式7. 由CF3SO2OCF3衍生的三氟甲醇盐在钯催化下对烯烃的三氟甲氧基化反应

Scheme 7. Palladium-catalyzed trifluoromethoxylation of alkenes with trifluoromethoxides derived from CF3SO2OCF3

图式8. 由CF3SO2OCF3衍生的AgOCF3对α-重氮羧酸酯的三氟甲氧基化反应

Scheme 8. Trifluoromethoxylation of α-diazo carboxylates with AgOCF3 derived from CF3SO2OCF3

图式9. CF3SO2OCF3对喹啉和菲啶N-氧化物的三氟甲氧基化反应

Scheme 9. Trifluoromethoxylation of quinoline N-oxides and phenanthridine N-oxides with CF3SO2OCF3

图式10. 由CF3SO2OCF3衍生的AgOCF3对醇类化合物的脱羟三氟甲氧基化反应

Scheme 10. Dehydroxytrifluoromethoxylation of alcohols with AgOCF3 derived from CF3SO2OCF3

图式11. 由CF3SO2OCF3衍生的AgOCF3对芳基重氮盐的三氟甲氧基化反应

Scheme 11. Trifluoromethoxylation of aryldiazonium salts with AgOCF3 derived from CF3SO2OCF3

图式12. CF3SO2OCF3与胺类化合物的点击反应

Scheme 12. Click reaction of amines with CF3SO2OCF3

图式13. CF3SO2OCF3对羧酸的脱羟氟化反应

Scheme 13. Dehydrofluorination of carboxylic acids with CF3SO2OCF3

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