Chemistry of Iminium Salts and Related Compounds

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Synthesis of a family of 3-alkyl- or 3-aryl-substituted 1,2-dihydroquinazolinium salts and their isomerization to 4-iminium-1,2,3,4-tetrahydroquinolines.

A straightforward synthesis of substituted 1,2-dihydroquinazolinium triflates (3) is reported by reaction of 2-imino-substituted anilines with a range of carbonyl compounds in the presence of triflic acid via intermediate iminium salts. Similar reactions with di- or trialdehydes and triflic acid give bis- or tris-(1,2-dihydroquinazolinium) salts. Some 4-methyl substituted 1,2-dihydroquinazolini...

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One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxid...

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Enaminosulfones from 3-Trifloxypropene Iminium Salts: A 1,5(O5C) Trifluoromethylsulfonyl Shift*

Triflic anhydride (Tf2O) is the reagent of choice for the introduction of the trifluoromethylsulfonyl (CF3SO2) group into a variety of organic substrates, and the resulting compounds often have a unique chemical reactivity [1]. A case in point is given by 3-trifloxypropene iminium triflates which are obtained by O-sulfonylation of enaminones with Tf2O [2, 3] and which are suited for transformat...

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تاریخ انتشار 2012