Electrochemically InducedN-Alkylation of Pyrroles

Feroci, Marta; Inesi, Achille; Rossi, Leucio; Sleiter, G.

doi:10.1002/(sici)1099-0690(199904)1999:4<955::aid-ejoc955>3.0.co;2-3

Cited by 14 publications

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“…Our main interest in imidazolium ionic liquids is their use in electroorganic synthesis, as solvents and precursors of N-heterocyclic carbenes (NHCs). In fact, the monoelectronic electrochemical reduction of an imidazolium cation leads to the formation of the corresponding NHC (Scheme 1), [19][20][21][22][23][24][25] which can behave as a base and/or as a nucleophile depending on the reaction partner. [26][27] NHCs are among the most popular organocatalysts, [28][29] mainly when an aldehyde is involved.…”

Section: Introductionmentioning

confidence: 99%

Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer

et al. 2019

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The cathodic reduction of dicationic imidazolium bromides, whose spacer is either an aliphatic chain or a xylyl group, leads to the formation of the corresponding N‐heterocyclic carbenes (NHCs), which were isolated as the corresponding thiones, after reaction with elemental sulfur. The behaviour of the dications was compared with the corresponding monocations. The behaviour of dicarbenes depends on the nature of the spacer. This study evidenced that dicarbenes deriving from xylyl dications are less stable than the corresponding aliphatic ones (giving lower yields in thiones), due to a debenzylation reaction. On the other hand, the yields in thiones starting from aliphatic dications are higher than the corresponding monocations, suggesting a cooperative reduction at the electrode of the two imidazolium moieties. The cathodic process was confirmed using the co‐electrogenerated hydrogen to reduce 2,2,2‐trifluoroacetophenone to the corresponding alcohol.

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Section: Introductionmentioning

confidence: 99%

Cathodic Behaviour of Dicationic Imidazolium Bromides: The Role of the Spacer

et al. 2019

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“…Surprisingly, to the best of our knowledge, there is no report dealing with 1,3-disubstituted 4-nitropyrrole having a carbonyl group at the 2-position except for a single description . This fact encouraged us to investigate the ring transformation of nitroisoxazolone 2a with 1,3-dicarbonyl compounds affording a new class of compounds, 2,3-difunctionalized 4-nitropyrroles.…”

Section: Introductionmentioning

confidence: 99%