New stereoselective $$C_{sp^2 } - C_{sp^3 }$$ coupling: Catalytic iodomethylation of acetylene with methyl iodide into E-1-iodopropene

Митченко, С. А.; Khazipov, Oleg V.; Krasnyakova, T. V.

doi:10.1134/s0023158414030094

Cited by 4 publications

(2 citation statements)

References 14 publications

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“…Facile substitution of the π -bonded acetylene with free olefins or CO results, respectively, in alkene-alkenyl 145 or carbonyl-alkenyl 146 complexes ( Scheme 77 ). In some cases, it is possible to isolate Pt-containing intermediates with acetylene to study kinetics and other properties [ 182 ].…”

Section: Acetylene In Organic Synthesismentioning

confidence: 99%

Acetylene in Organic Synthesis: Recent Progress and New Uses

et al. 2018

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Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule.

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Section: Acetylene In Organic Synthesismentioning

confidence: 99%

Acetylene in Organic Synthesis: Recent Progress and New Uses

et al. 2018

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“…[19,20] Due to the relatively lower activity and shorter lifetime of non-metallic catalysts, some distance remains from industrialization. As for metal catalysts, a series of metal chlorides, including Pt 4 + , [8,[21][22][23] Pd 2 + , [21,[24][25][26][27] Ru 2 + , [12,[28][29][30][31][32] Cu 2 + , [33,34] Sn 2 + , [35] have been explored as potential Hg-free catalysts, but Au-based catalysts possessing a higher standard reduction potential are considered as the most promising replacement. [4,[36][37][38][39] The coking deposition and the agglomeration or the reduction of active species are the main reasons for the deactivation of Au-based catalyst, which have been briefly introduced in the previous literatures.…”

Section: Introductionmentioning

confidence: 99%

Hydrochlorination of Acetylene Over the Activated‐Carbon‐Supported Au Catalysts Modified by N−P−O‐Containing Ligand

Zhang

et al. 2019

ChemCatChem

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Etidronic acid (HEDP) and Nitrilotri(methylphosphonic acid) (ATMP) were selected as heteroatoms-containing ligands to modify Au catalysts for acetylene hydrochlorination. Results from several analytical methods reveal an optimal mole ratio of Au/ligand (L) of 1 : 1, with obvious increments over the Au 1 -L 1 / AC catalyst. The coordination between the Au and the heteroatoms, especially the collocative presence of N, P, and O promoted electron transfer from the heteroatoms to the Au n + and increased the density of the electron cloud around active centers. This stabilized the Au n + and increased the difficulty in the reduction of Au species, and re-oxidized the Au 0 to active Au n + species. Moreover, the coordination inhibited the migration of active components. The increased density of the electron cloud around active centers also weakens the adsorption capacity for C 2 H 2 and strengthens the adsorption ability for HCl of the catalysts, which is conductive for constructing the micro-environment favorable to the reaction. DFT calculations proved the stabilization effect of the heteroatoms-containing ligands, and the energy sequence of the transition states supported the experimental results.

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Addition Reactions: Polar Additions

Knipe¹

2019

Organic Reaction Mechanisms Series

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New stereoselective $$C_{sp^2 } - C_{sp^3 }$$ coupling: Catalytic iodomethylation of acetylene with methyl iodide into E-1-iodopropene

Cited by 4 publications

References 14 publications

Acetylene in Organic Synthesis: Recent Progress and New Uses

Acetylene in Organic Synthesis: Recent Progress and New Uses

Hydrochlorination of Acetylene Over the Activated‐Carbon‐Supported Au Catalysts Modified by N−P−O‐Containing Ligand

Addition Reactions: Polar Additions

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