A silver-catalyzed cascade cyclization reaction of isocyanides with sulfoxonium ylides has been developed for the first time. This reaction provides a new and efficient method for the construction of highly functionalized 3-aminofurans and 4-aminoquinolines from readily available starting materials in a single step.
A novel method for the synthesis of trifluoroethyl-substituted imidazoles is reported via a rhodium-catalyzed three-component reaction of isocyanides, 2,2,2-trifluorodiazoethane and activated methylene isocyanides or azomethine ylides.
The DBU-catalyzed [3 + 3] and [3 + 2] cyclization reactions of azomethine ylides with adiazocarbonyls as N-terminal electrophiles have been developed. These reactions involve a sequential intermolecular nucleophilic addition/intramolecular cyclization/oxidation procedure. By the assembly of readily available starting materials, these transformations offer novel, highly efficient one-pot syntheses of various functionalized 1,2,4-triazine and 1,2,4-triazole derivatives in an atom-economical manner under ambient and metal-free conditions in a high regio-and diastereoselective manner.
A photocatalyst-free radical cleavage of α-diazo
sulfonium
salts has been developed for the first time. The reaction provides
an efficient method for the generation of diazomethyl radicals from
α-diazosulfonium triflates under photochemical conditions. Utilizing
the in situ generated diazomethyl radicals as key intermediate, the
coupling cyclization reaction of α-diazosulfonium triflates
with α-oxocarboxylic acids or alkynes has been achieved. The
method affords a diverse set of important 2,5-disubstituted 1,3,4-oxadiazoles
and 3,5-disubstituted-1H-pyrazoles with excellent
regioselectivity in a single step. A reaction mechanism involving
a radical pathway was further supported by control experiments and
DFT calculations.
A zinc-catalyzed three-component reaction of isocyanides, α-diazoketones, and anhydrides has been realized as a novel and efficient method for the synthesis of polysubstituted maleimides.
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