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Alkoxycarbonylation and amidation of aryl iodides catalyzed by palladium complexes

Journal Article · · Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States)
OSTI ID:6227411
; ;
The authors report their results concerning the carbonylation of aryl iodides in the presence of various types of metal alkoxides, such as Et/sub 3/SnOMe, Al(OPr)/sub 3/, Mg(OMe)/sub 2/, and NaOMe, as well as in the presence of a tin amide, Me/sub 3/SnNET/sub 2/. In order to determine the optimum conditions for the reaction process, they first investigated the effect of solvent and Pd catalyst on the alkoxycarbonylation of 4-NO/sub 2/C/sub 6/H/sub 4/I. The tin derivative Et/sub 3/SnOMe was used as the nucleophilic reagent. Reaction progress was followed by the disappearance of the starting material and also by the formation of the reaction product, 4-NO/sub 2/C/sub 6/H/sub 4/CO/sub 2/Me. Tin and sodium alkoxides, as well as tin amides, can be used as coreagents in the palladium complex-catalyzed carbonylation of aryl iodides. The use of such powerful nucleophiles as metal alkoxides and amides permits the carbonylation reactions to be carried out under milder conditions and at faster rates than those described in the literature. A mechanism for the alkoxycarbonylation and amidation of aryl halides has been proposed based on results obtained using stoichiometric reactions of palladium complexes.
Research Organization:
M.V. Lomonosov Moscow State Univ., USSR
OSTI ID:
6227411
Journal Information:
Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States), Journal Name: Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.); (United States) Vol. 35:7; ISSN BACCA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPLEXES
ALKALINE EARTH METAL COMPLEXES
ALKOXIDES
ALUMINIUM COMPLEXES
AMIDES
AMINATION
AROMATICS
CARBON COMPOUNDS
CARBON MONOXIDE
CARBON OXIDES
CARBONYLATION
CATALYSTS
CATALYTIC EFFECTS
CHALCOGENIDES
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CHROMATOGRAPHY
COMPARATIVE EVALUATIONS
COMPLEXES
HALIDES
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
INFRARED SPECTRA
IODIDES
IODINATED AROMATIC HYDROCARBONS
IODINE COMPOUNDS
MAGNESIUM COMPLEXES
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
PALLADIUM CHLORIDES
PALLADIUM COMPLEXES
PALLADIUM COMPOUNDS
PALLADIUM IODIDES
PROMOTERS
SEPARATION PROCESSES
SODIUM COMPLEXES
SPECTRA
STOICHIOMETRY
TIN COMPLEXES
TRANSITION ELEMENT COMPLEXES
TRANSITION ELEMENT COMPOUNDS
ULTRAVIOLET SPECTRA