Synthesis of α-Diketones from Alkylaryl- and Diarylalkynes Using Mercuric Salts
نویسندگان
چکیده
Both alkylarylalkynes and diarylalkynes 1 are converted into the α-diketones 2 in good yield by the use of mercuric salts, e.g., mercuric nitrate hydrate or mercuric triflate, in the presence of water. Other mercuric salts, e.g., sulfate, chloride, acetate, or trifluoroacetate, do not provide the diketone product. A possible mechanism is proposed.
منابع مشابه
Wacker-type oxidation of alkynes into 1,2-diketones using molecular oxygen.
An intriguing new Wacker-type oxidation of alkynes catalyzed by PdBr(2) and CuBr(2) is described, which opens an efficient access to 1,2-diketones using molecular oxygen. Under the optimized conditions, a variety of alkynes, including diarylalkynes, arylalkylalkynes, and dialkylalkynes, were compatible substrates in this transformation. The mechanism of this reaction was preliminarily investiga...
متن کاملNHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones
Thiazolium carbene-catalyzed reactions of 1,2-diketones and 1,2,3-triketones with enones and ynones have been investigated. The diketones gave α,β-double acylation products via unique Breslow intermediates isolable as acid salts, whereas the triketones formed stable adducts with the NHC instead of the coupling products.
متن کاملGold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles
A gold-catalyzed oxidation of arylallenes to form α-diketones and aldehydes in good yields is presented. Further directed synthesis of quinoxalines and benzimidazoles, via the condensation of the resulting α-diketones and aldehydes with benzene-1,2-diamine, was achieved in high yields.
متن کاملMicrowave Assisted Synthesis of N-Benzylenaminones Catalyzed by Chloroacetic acid
Benzylaminoalkenones and benzylaminoalkenoates 3 were synthesized from reaction of benzylamine with corresponding 1,3-diketones and 1,3-ketoesters in the presence of catalytic amount of chloroacetic acid under microwave radiation. This method offers several advantages including high yield of products, recyclable of the catalyst and easy experimental work-up procedure.
متن کاملAn investigation into the synthesis of an optically active trityl system
Several possible routes to obtain an optically active trityl system have been studied. Model systems, using triphenylcarbinol and 4-bromo-^1-chlorotriphenylcarbinol, were employed. Several routes to break down the glycolic acid derivatives of these alcohols were studied. These involve the preparation of the silver salt of the acid and its reaction with bromine; the reaction of the acid with mer...
متن کامل