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
TL;DR: In this article, 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 arenes sulfonyl azides with terminal alkynes in the presence of azodiisobutyronitrile.
Abstract: 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.
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TL;DR: Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved and provides a green approach to N-sulfonylamidines under mild conditions.
30 citations
TL;DR: 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.
Abstract: 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.
28 citations
TL;DR: In this article, a highly active catalyst based on copper iodide nanoparticles supported on magnetic aminomethylpyridine functionalized cellulose has been synthesized and characterized, and 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.
Abstract: 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.
25 citations
TL;DR: 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 as mentioned in this paper.
Abstract: 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.
15 citations
TL;DR: In this article, 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.
Abstract: 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.
14 citations
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TL;DR: Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously and has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects.
Abstract: Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.
1,479 citations
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400 citations
TL;DR: Two plausible mechanistic pathways involving ketenimine or triazole intermediate are tentatively presented for the copper-catalyzed three-component coupling reactions.
Abstract: A highly efficient, mild, practical, and catalytic multicomponent reaction for the synthesis of N-sulfonylamidines has been developed. This reaction has an extremely wide scope with regard to all three coupling components of alkyne, sulfonyl azide, and amine. Two plausible mechanistic pathways involving ketenimine or triazole intermediate are tentatively presented for the copper-catalyzed three-component coupling reactions.
384 citations
TL;DR: It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mild conditions.
Abstract: It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mild conditions. The present route is quite general, and a wide range of alkynes and sulfonyl azides are readily coupled catalytically with water to furnish amides in high yields. A variety of labile functional groups are tolerated under the conditions, and the reaction is regioselective in that only terminal alkynes react while double or internal triple bonds are intact. The reaction can be readily scaled up and is also adaptable to a solid-phase procedure with high efficiency.
379 citations