Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines

Novikov, Maxim A.; Ibatov, Yaroslav A.; Volchkov, N. V.; Lipkind, M. B.; Semenov, S. E.; Нефедов, О. М.

doi:10.1016/j.jfluchem.2017.01.001

Cited by 12 publications

(3 citation statements)

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“…In 2017, Nefedov, Novikov, and co-workers developed the copper-catalyzed ring-opening amination of gembromofluorocyclopropanes. 92 Once again, a copper(I) species allowed the isomerization of gem-bromofluorocyclopropanes to give 2-fluoroallylic bromides, and nucleophilic substitution of the halide by a N-nucleophile afforded the monofluoroalkenes (Scheme 74).…”

Section: Scheme 74 Cu-catalyzed Ring Opening Of Gem-bromofluorocyclopmentioning

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 74 Cu-catalyzed Ring Opening Of Gem-bromofluorocyclopmentioning

confidence: 99%

“…2-fluoroallylamines in good to high yields (Scheme 224). 92 Alternatively, the ring-opening isomerization and the nucleophilic substitution can be carried out as two individual steps. In the one case reported, this led to an increased yield.…”

Section: Review Syn Thesismentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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“…Among numerous fluorine-containing compounds, monofluoroalkene is of particular importance because alkene is ubiquitous in bioactive molecules [12][13][14][15][16][17] and materials [18][19][20][21]. Moreover, fluoroalkenes could also serve as fluorinated building blocks for further organic transformations [22][23][24][25][26]. Therefore, this entry will focus on the preparation of mono-or difunctionalized alkenyl fluorides from readily available alkyne precursors.…”

Section: Introductionmentioning

confidence: 99%