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Phenylacetylene is a prototypical terminal acetylene, undergoing many reactions expected of that functional group. It undergoes semi hydrogenation over Lindlar catalyst to give styrene . In the presence of base and copper(II) salts, it undergoes oxidative coupling to give diphenylbutadiyne . [ 6 ]
An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. [1] Being a cycloaddition reaction, it has high atom economy.
The reaction provides a means to generate alkynes from alkenes, which are first halogenated and then dehydrohalogenated. For example, phenylacetylene can be generated from styrene by bromination followed by treatment of the resulting of 1,2-dibromo-1-phenylethane with sodium amide in ammonia: [9] [10]
These reactions invariably involve metal-acetylide intermediates. This reaction was discovered by chemist John Ulric Nef in 1899 while experimenting with reactions of elemental sodium, phenylacetylene, and acetophenone. [3] [4] For this reason, the reaction is sometimes referred to as Nef synthesis.
Phenylacetylene was proven to form Pd monoacetylide complex D as well as Pd bisacetylide complex F under mild reaction conditions. Both activated species, namely complexes B and F , are involved in the transmetallation step, forming complex C and regenerating D .
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The reaction is attractive for their atom economy because it avoid pre-functionalized starting materials often required in traditional redox-neutral cross-couplings. Oxidative phenol couplings, however, often suffer from over-oxidation, especially since the intended coupled product is more oxidizable (has a lower oxidation potential ) than the ...
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