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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 ]
Yet another method involves the coupling of iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling. The related Sonogashira coupling involves the coupling of iodobenzene and phenylacetylene. Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers. [1]
It is a member of the diyne chemical class and can be made via the Glaser coupling of phenylacetylene [2] However, a variety of other synthesis methods have been developed. [3] [4] Diphenylbutadiyne forms a variety of metal-alkyne complexes. One example is the organonickel complex (C 5 H 5 Ni) 4 C 4 (C 6 H 5) 2. [5]
Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride. [3] Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of 1,3-butadiyne. [4]
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A recyclable polymeric phosphine ligand is obtained from ring-opening metathesis polymerization of a norbornene derivative, and has been used in the copper co-catalyzed Sonogashira reaction of methyl p-iodobenzoate and phenylacetylene using Pd(dba) 2 ·CHCl 3 as a palladium source. [38]