2020
DOI: 10.1021/acscatal.0c00988
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Abstract: 1,3-Enynes are core structures of various natural products or pharmaceuticals and are broadly used synthons in organic synthesis. Metal-catalyzed alkyne dimerization is a desirable preparation method, due to its perfect atom economy and the readily available alkyne substrates. Controlling the regio- and stereoselectivity remains a challenge, due to the competing formation of the head-to-tail (gem) and head-to-head (E/Z) isomers. Although catalytic systems based on noble metals have been extensively studied, th… Show more

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Cited by 41 publications
(27 citation statements)
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“…Intermolecular carbon-carbonb ondf orming reactions are amongstt he most covetedd isconnections in synthetic organic chemistry.A sac onceptually straightforward and atom economical method for the preparationo fc onjugated 1,3-enynes, the transition metal catalysed dimerisationo ft erminala lkynes is an exampleo fg rowing importance. [1,2] These enynes are versatile unsaturated synthons and key subunits of biologically active compoundsa nd functional materials, however,t heir selective formationr emains difficult to realise. In addition to competing metal-catalysed reactions of terminal alkynes, that can lead to ar ange of alternative unsaturated products, [3,4] the formal addition of the C(sp)ÀHb ond of one alkyne across the CCb ond of another is ap rocess that can resulti nt hree different 1,3-enyne isomersb yv irtue of head-to-tail (gem-) or head-to-head coupling (E-a nd Z-) as depicted in Scheme 1.…”
Section: Introductionmentioning
confidence: 99%
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“…Intermolecular carbon-carbonb ondf orming reactions are amongstt he most covetedd isconnections in synthetic organic chemistry.A sac onceptually straightforward and atom economical method for the preparationo fc onjugated 1,3-enynes, the transition metal catalysed dimerisationo ft erminala lkynes is an exampleo fg rowing importance. [1,2] These enynes are versatile unsaturated synthons and key subunits of biologically active compoundsa nd functional materials, however,t heir selective formationr emains difficult to realise. In addition to competing metal-catalysed reactions of terminal alkynes, that can lead to ar ange of alternative unsaturated products, [3,4] the formal addition of the C(sp)ÀHb ond of one alkyne across the CCb ond of another is ap rocess that can resulti nt hree different 1,3-enyne isomersb yv irtue of head-to-tail (gem-) or head-to-head coupling (E-a nd Z-) as depicted in Scheme 1.…”
Section: Introductionmentioning
confidence: 99%
“…[1] Indeed, althoughawide variety of catalysts-based on transi-tion metals,l anthanides, actinides, and main group elementshave been shown to promotet hese reactions, few are capable of producing single enyne isomers with high fidelity;t he majority lead to mixtures of regio-or stereo-isomers. [1] Greater mechanistic understanding of these reactions is therefore required to enable rational design of more effective catalysts and promote furthera pplication of terminal alkyne coupling reactions in organic synthesis.…”
Section: Introductionmentioning
confidence: 99%
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