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Updated: Jun 17, 2026
Synthesis and Catalytic Performance of Gold Intercalated in the Walls of Mesoporous Silica
Published on: July 9, 2015
Synthesis and biological studies of some gold(I) complexes containing functionalised alkynes
Esther Schuh1, Seied M Valiahdi, Michael A Jakupec
1Fachbereich C, Anorganische Chemie Bergische Universität Wuppertal, Gaussstr. 20, D-42929, Wuppertal, Germany.
Abstract:
The propargyl ethers 7-chloro-(4-propargyloxy)quinoline, 1-propargyloxynaphthalene and 2-propargyloxybenzophenone react with [AuCl(PPh(3))] in the presence of KOH to give the gold(I) alkynyl complexes [Au(C[triple bond]COCH(2)Ar)(PPh(3))] in good yields. The compounds were fully characterised by spectroscopic methods and were subsequently examined for their biological activity against four tumour cell lines as well as their activity against Plasmodium falciparum, the parasite responsible for malaria. The compounds show antiproliferative effects in human cancer cells with IC(50) values ranging from 0.4-12 microM.
Related Concept Videos
02:27Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
02:37Structure and Physical Properties of Alkynes
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The simplest alkyne is ethyne, or...
02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.