Nucleophilic fluorination of alkynyliodonium salts by alkali metal fluorides: access to fluorovinylic compounds

Nguyen, Thi-Huu; Abarbri, Mohamed; Guilloteau, Denis; Mavel, Sylvie; Emond, Patrick

doi:10.1016/j.tet.2011.03.043

Cited by 21 publications

(14 citation statements)

References 43 publications

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“…In 2011, Emond and co-workers reported the nucleophilic fluorination of alkynyliodonium salts with cesium fluoride, where the latter was the limiting reagent. 23 Subsequent reduction with NaBH 4 in a one-pot procedure delivered the expected fluoroalkene in modest to good yield (Scheme 23). Alternatively, the intermediate vinyliodonium salt was isolated prior to reduction (see Table 10,…”

Section: Scheme 16mentioning

confidence: 99%

“…Emond and co-workers reported the synthesis of 2-fluorovinyliodonium salts from alkynyliodonium salts in the presence of cesium fluoride. 23 This fluoride source was chosen as it gave good regio-and stereoselectivity ( Table 10). The use of alkynyliodonium tetrafluoroborate salts gave better results than the corresponding tosylates in this transformation.…”

Section: Scheme 83 Gold-catalyzed Hydrofluorination Of Iodoacetylenesmentioning

confidence: 99%

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Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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Section: Scheme 16mentioning

confidence: 99%

Section: Scheme 83 Gold-catalyzed Hydrofluorination Of Iodoacetylenesmentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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“…In 2011, Nguyen, Emond, and their collaborators reported an optimized method for the synthesis of (Z)-2-fluoroalkenyliodonium salts using CsF as the fluorine source (Fig. 10) [31]. Additionally, they developed a one-pot-two-reaction method to give vinyl fluoride compounds with good yields by introducing NaBH 4 as a reducing agent to remove the iodonium group.…”

Section: Synthesis Of Multifunctionalized Fluoroalkenes Via Aryl-alkementioning

confidence: 99%

Fluorination of Aryl-Alkenyl-Iodonium Salts for Preparing Alkenyl Fluorides

Qü

Li²

2017

Fluorination

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“…Although the fluorinated alkenes 4a,b were obtained in low yields (15-20 %), these initial results showcased the potential of such an approach. [11] In 2007, Sadighi and co-workers [12] employed electrophilic (NHC)gold(I) complexes to catalyze the trans-hydrofluorination of internal alkynes 5a-f at room temperature (Scheme 3). Indeed, by using 20 % aqueous HF, fluoroalkenyliodonium salts bearing functional groups such as a carbonyl group (4c) and halogen (4d) were synthesized in good yields and with high stereoselectivities towards the Z iso-mer.…”

Section: Direct Introduction Of Fluorinated Groups With Concomitant Fmentioning

confidence: 99%