The association of trifluoromethyl(-CF3) group to chalcogens has led to new fluorinated substitutes with interesting electronic and physico-chemical properties, which presented themselves in a large panel of various applications in the fields from pharmaceuticals to material science. Currently, the incorporation of -OCF3 and-SCF3 moieties have been relatively well-developed due to their unique and specific properties (such as high lipophilicity, positively contributing to the bioavailability of molecules.). However, studies on the construction of the C-SeCF3 bond are less reported and investigated, despite that the trifluoromethylselenyl group (the association of CF3 group to next chalcogen[Selenium]) may also have potential biological properties as -OCF3 and -SCF3 groups.
After "intermittent" developments from pioneer approaches in the late 60's to these last years, the introduction of SeCF3 group into organic compounds has been emerged with promising progress. Some modern and efficient methods have been established and empolyed to obtain trifluoromethylselenolated molecules recently. In particular, the development of new bench-stable,operationally-simple trifluoromethylselenolating reagents should be importantly complemental tools in the synthestic toolbox for organic chemists by providing more fluorinated compounds with specific properties and new applications.
All the methods for indirect or direct introduction of Se-CF3 moiety can be divided into three types of electrophilic,radical and nucleophilic reactions.
1. Electrophilic Trifluoromethylselenolation: Trifluoromethylselenyl chloride (CF3SeCl,kumi3F50) was previously commonly employed for electrophilic trifluoromethylselenolationto react with electron rich arenes(anilines derivatives, phenol) and diethyl malonate sodium salt, but the usage of this reagent was somewhat limited due to its low boiling point(22-31°C) and potential toxicity. In order to limit any contact with CF3SeCl, Tlili group has recently developed a one-pot two-step protcol to introduce the SeCF3 group into a large varity of nucleophilies, by utilizing the electrophilic reagent of Benzyl(trifluoromethyl)selenide(kumi3F51). In order to overcome the volatility of CF3SeCl, Tlili group continuously designed a new, bench-stable and easy-to-handle reagent,Trifluoromethyl tolueneselenosulfonate(kumi3F52), which has been reportedly employed to trifluoromethylselenolate aryl boronic acid in a electrophilic route.
2. Radical Trifluoromethylselenolation: Billard and Langlois recently demonstrated that the Langlois reagent(CF3SO2Na,kumi3F19) can be used as a radical trifluoromethyl source to react with diphenyldiselenide in a mild term with a very good yield of desired PhSeCF3.
3. Nucleophilic Trifluoromethylselenolation: Nucleophilic trifluoromethylselenolating reagents are basically stabilized by metal(σ-bonded SeCF3) or with ammonium salts. Trifluoromethylselenocopper(I) ([Cu]SeCF3,kumi3F48) is the most empolyed reagent with a limited substrate scope for direct nucleophilic trifluoromethylselenolation reactions in recent years. In the early year of 2000s, Tyrra group firstly reported the synthesis of Tetramethyl ammonium trifluoromethylselenate ([Me4N]SeCF3,kumi3F54), but the its use as a SeCF3 donor has only been expolited, more recently, by other research groups in the trifluoromethylselenolation of various substrate scope such as (hetero)aromatic amines,terminal alkynes,aryl bronic acids drivatives,(hetero)aryl halides, and α-diazo esters,etc.. Most recently, Weng group has developed a family of discrete copper(I) trifluoromethylselenats complexes. 2,2'-bipyridine)Cu(trifluoromethylselenolate) ([byp]Cu[SeCF3],kumi3F55) is the most active and efficient copper complex,which was reportly reacting with a wide range of substrates, including aryl halides,alkyl halides,α-bromo-α,β-unsaturated carbonyl compounds,propargylic chlorides, allylic bromides,vinyl halide derivatives,terminal alkynes,heterocyclicaryl bromides,acid chlorides and 3-iodo-2-pyrones,etc..
Trifluoromethylselenolating Reagents Overview
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