The development of 11C-carbonylation chemistry: A systematic view
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The prospects for using carbon-11 labelled compounds in molecular imaging has improved with the development of diverse synthesis methods, includingKeywords:
Carbonylation
A systematic account of data concerning the problems of the synthesis of a wide variety of organic and organosilicon derivatives of carbonic acid (chlorocarbonates, carbonates, isocyanates, carbodiimides, acylcarbamoyl chlorides, etc.) by the reaction of phosgene with N- and O-silyl-substituted amines, amides, diazoles, iminoesters, and ethers derived from alcohols, glycols, etc. is given for the first time. The bibliography includes 113 references.
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Carbonic acid
Hydrofluoric acid
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The reaction of enynes with aldehydes in the presence of a catalytic amount of [RhCl(cod)](2)/dppp results in the Pauson-Khand-type reaction without the use of gaseous carbon monoxide to give bicyclic cyclopentenones in high yields (14 examples). Aldehydes serve as a source of carbon monoxide, and their carbonyl moiety is transferred to enynes, resulting in the formation of the carbonylated products. This reaction represents the first example of a CO-transfer carbonylation.
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Moiety
Pauson–Khand reaction
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Recent progress, with some emphasis on the author's own work, on the understanding of the mechanism of the reductive carbonylation of nitroarenes and of the oxidative carbonylation of amines is discussed, highlighting the close connection between the two reactions and trying to unify scattered data in the literature. Isocyanates, carbamates and ureas can be obtained by either procedure, without the need for the use of the toxic and corrosive phosgene.
Carbonylation
Protein Carbonylation
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The methods of synthesis of organic compounds by the carbonylation of acetylene, diene, and alkene hydrocarbons as well as alcohols in the presence of homogeneous and heterogeneous catalysts based on Group VIII metals and acid catalysts are examined. Data are presented on the synthesis of unsaturated and saturated mono- and di-carboxylic acids and their esters, lactones, and ketones from hydrocarbons and alcohols as well as the activities, selectivities, and stabilities of the catalytic systems in the carbonylation reaction. The bibliography includes 256 references.
Carbonylation
Alkene
Acetylene
Homogeneous Catalysis
Diene
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Carbonylation chemistry (carbon monoxide chemistry) has been the subject of extensive research in labo-scale organic syntheses as well as industrial processes, since it provides a powerful tool for the direct synthesis of a wide variety of carbonyl-containing compounds. However, the methods suffer from major disadvantages, including the high toxicity of carbon monoxide and difficulties in handling this gaseous reagent. The review describes innovative strategies to solve these drawbacks. The strategies should provide many synthetic organic chemists with experimentally simple and safe tools for carbonylation.
Carbonylation
Monoxide
Organic Synthesis
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Nickel seems one of the most promising transition metals as a catalyst for a variety of carbonylation reactions. In fact, it has played an important role in industrial usage. However, a limited number of the catalytic carbonylation reactions have been reported. One of the reasons why chemists would not develop nickel-catalyzed carbonylation reactions is due to the possibility of the formation of the notorious highly toxic Ni(CO)4 in situ, which indicates that nickel can react with carbon monoxide. In this chapter, formation of nickelacycles and their reactivity with carbon monoxide to give cyclic carbonyl compounds are introduced.
Carbonylation
Reactivity
Monoxide
Nickel compounds
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W(CO)6-catalyzed carbonylation provides an alternative to phosgene or phosgene derivatives such as 1,1-carbonyldiimidazole (CDI) for the conversion of amines to ureas. As an illustration, the core structure of the HIV protease inhibitors DMP 323 and DMP 450 has been prepared by catalytic carbonylation of diamine intermediates from the original syntheses.
Carbonylation
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Superbase
Carbonylation
Pyrrole
Carbonic acid
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Abstract Progress in organometallic catalysis began with the discovery of the Roelen reaction (hydroformylation with carbon monoxide and hydrogen) in 1938 and the Reppe reaction (hydrocarboxylation with carbon monoxide and water) in 1939. Since then, carbonylation chemistry by using carbon monoxide has occupied a central position in organometallic chemistry, as it relates to organic synthesis. There is, however, the problem of using gaseous carbon monoxide (a toxic greenhouse gas) in this chemistry. Recently, some strategies that address this issue have appeared. This minireview describes carbonylation reactions that can be conducted without the direct use of carbon monoxide. These carbonylation reactions provide reliable and accessible tools for synthetic organic chemists.
Carbonylation
Organometallic Chemistry
Monoxide
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