Regio- and Stereoselective N-addition to an Open Bromo Vinyl Cation

Chuchmareva, Marina; Strauch, Christina; Schröder, Sebastian; Collong, Arndt; Niggemann, Meike

doi:10.1016/j.tetlet.2021.153173

Cited by 9 publications

(10 citation statements)

References 37 publications

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“…LiNTf2 48 and Bu4NNTf2 to increase the solubility of LiNTf2 48. The regioselectivity of the addition is determined by the cation-stabilizing effect of the α-aryl substituent [108]: (Scheme 16). For electron-deficient 4-cyanophenol, the only observed product was the product of O-alkylation, while for X = halogen and electron-releasing substituents, after 1 h, a mixture of C-and O-alkylated products was formed, and after 20 h, only the C-alkylation products were observed in the mixture.…”

Section: Gold Triflimidementioning

confidence: 99%

“…LiNTf2 48 and Bu4NNTf2 to increase the solubility of LiNTf2 48. The re oselectivity of the addition is determined by the cation-stabilizing effect of the α-aryl su stituent [108]: (Scheme 16). N-vinyl triflimides were first described in the work [107].…”

Section: Gold Triflimidementioning

confidence: 99%

“…LiNTf2 48 and Bu4NNTf2 to increase the solubility of LiNTf2 48. The re oselectivity of the addition is determined by the cation-stabilizing effect of the α-aryl su stituent [108]: (Scheme 16). In the presence of calcium triflimide 66, the annulation reaction of an aldehyde amine 62, alkene 63 and alkyne 64 takes place.…”

Section: Gold Triflimidementioning

confidence: 99%

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Triflamides and Triflimides: Synthesis and Applications

Moskalik

Astakhova

2022

Molecules

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Among the variety of sulfonamides, triflamides (CF3SO2NHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties. Their strong electron-withdrawing properties and low nucleophilicity, combined with their high NH-acidity, makes it possible to use triflamides in a vast variety of organic reactions. This review is devoted to the synthesis and use of N-trifluoromethanesulfonyl derivatives in organic chemistry, medicine, biochemistry, catalysis and agriculture. Part of the work is a review of areas and examples of the use of bis(trifluoromethanesulfonyl)imide (triflimide, (CF3SO2)2NH, Tf2NH). Being one of the strongest NH-acids, triflimide, and especially its salts, are widely used as catalysts in cycloaddition reactions, Friedel–Crafts reactions, condensation reactions, heterocyclization and many others. Triflamides act as a source of nitrogen in C-amination (sulfonamidation) reactions, the products of which are useful building blocks in organic synthesis, catalysts and ligands in metal complex catalysis, and have found applications in medicine. The addition reactions of triflamide in the presence of oxidizing agents to alkenes and dienes are considered separately.

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Section: Gold Triflimidementioning

confidence: 99%

Section: Gold Triflimidementioning

confidence: 99%

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Triflamides and Triflimides: Synthesis and Applications

Moskalik

Astakhova

2022

Molecules

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“…1). [24,25] In their study, the reaction of internal alkynes such as 1-phenyl-1-hexyne gave the corresponding vinyl triflimides with high stereoselectivity. However, in the absence of LiPF 6 or Bu 4 NPF 6 , no product was obtained.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1‐amino‐3‐aryl Naphthalenes from Bis(perfluoroalkanesulfonyl)imide with 1,2‐diethynylbenzenes

Kawamoto,

Yamasaki,

Ikazaki

et al. 2024

Asian J Org Chem

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Although the synthesis of vinyl triflates has a long history, the synthesis of vinyl bis(perfluoroalkanesulfonyl)imides has not been reported yet. Here, we report a simple synthetic route to vinyl bis(perfluoroalkanesulfonyl)imides that does not require any additives. The stereoselectivity originates from the steric hindrance between the aryl group and the imide. The reaction proceeds chemoselectively, and subsequent cyclization provides the 1‐amino‐3‐aryl naphthalene derivatives.

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“…7 To address this limitation, Niggemann and coworkers reported a system involving Brønsted/Lewis cooperative protonation of the alkyne triple bond to achieve alkyne hydroimidation under remarkably mild conditions. 8 Our own group recently reported the use of substituted pyridinium salts as proton sources for the formation of vinyl cations from alkyne substrates. 9 This tunable class of Brønsted acids provides a conceptually and operationally simple approach for the generation of vinyl cations from readily available alkyne starting materials.…”

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confidence: 99%