Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage.

A Pd-catalyzed and ligand-free carbonylation/cycloaddition/decarboxylation cascade synthesis of sulfonyl amidines from sulfonyl azides and substituted amides at low CO pressure is reported. The reaction proceeds via an initial Pd-catalyzed carbonylative generation of sulfonyl isocyanates from sulfonyl azides, followed by a [2 + 2] cycloaddition with amides and subsequent decarboxylation, which liberates the desired sulfonyl amidines, generating N2 and CO2 as the only reaction byproducts. Using this simple protocol, a diverse range of sulfonyl amidines was obtained in moderate to excellent yields. In addition, the reaction can also be directed through a more conventional amidocarbonylation pathway by employing N-monosubstituted amide nucleophiles to afford acyl sulfonyl ureas in good yields.

Synthesis of N-Sulfonyl Amidines and Acyl Sulfonyl Ureas from Sulfonyl Azides, Carbon Monoxide, and Amides

In this study, a highly active catalyst based on copper iodide nanoparticles supported on magnetic aminomethylpyridine functionalized cellulose has been synthesized and characterized. Its catalytic activity was investigated in the multicomponent synthesis of N-sulfonylamidines via an in situ generated sulfonyl ketenimine intermediate under solvent free conditions at room temperature. The desired products were obtained in good to excellent yields at short reaction times. Based on observed results, the synthesized catalyst was an efficient, magnetically separable, recyclable and green catalyst from a natural source.

Copper iodide nanoparticles supported on magnetic aminomethylpyridine functionalized cellulose: a new heterogeneous and recyclable nanomagnetic catalyst for facile access to N-sulfonylamidines under solvent free conditions

Copper exchanged Scolecite was successfully synthesized and used as an efficient, mild and recyclable catalyst for promoting multi-component synthesis of amidines from 4-toluenesulfonyl azide, phenyl acetylene and variety of substituted amines in THF at ambient temperature in good yields within short reaction time.

A modular approach for multicomponent synthesis of amidines using modified Scolecite

A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C–N bonds are constructed­ by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.

One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines To Access 2,3-Dihydro-1H-imi­dazo[1,2-a]indoles

A facile and efficient synthesis of N-sulfonyl-N,N-disubstituted amidines has been achieved via a CuI-catalyzed three-component free-radical coupling reaction of tertiary amines and arenesulfonyl azides with terminal alkynes in the presence of azodiisobutyronitrile (AIBN). The reaction mechanism of this reaction has also been studied.

Syntheses of N-sulfonyl-N,N-disubstituted amidines via a three-component free-radical coupling reaction of tertiary amines and arenesulfonyl azides with terminal alkynes

Wei Jiang

Papers

Syntheses of N-sulfonyl-N,N-disubstituted amidines via a three-component free-radical coupling reaction of tertiary amines and arenesulfonyl azides with terminal alkynes