Nickel or iron catalysed carbon-carbon coupling reaction of arylenes, alkenes and alkines

A catalyst and aryl technology, applied in the field of carbon-carbon bonds, can solve the problems of dehalogenation of aryl halides, no synthesis method found, etc.

Inactive Publication Date: 2008-11-05
SALTIGO GMBH
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Problems solved by technology

[5] Although very efficient cross-coupling reactions have been achieved between a large number of alkylmagnesium reagents and aryl halides or aryl sulfonates, catalytic cross-couplings between two aryl groups are problematic because Significant homo coupling reaction of arylmagnesium species and until now no synthetic approach to this problem has been identified
[5，6] But dehalogenation of aryl halides also occurs at the same time

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  • Nickel or iron catalysed carbon-carbon coupling reaction of arylenes, alkenes and alkines
  • Nickel or iron catalysed carbon-carbon coupling reaction of arylenes, alkenes and alkines
  • Nickel or iron catalysed carbon-carbon coupling reaction of arylenes, alkenes and alkines

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Embodiment

[0059] Unless otherwise indicated, all reactions were performed by magnetic stirring and in the case of air-sensitive or hygroscopic compounds under argon as the inert gas in annealed glassware. Syringes were used to transfer reagents and solvents were flushed with argon before their use. Reactions were controlled by gas chromatography (GC and GC-MS) or thin layer chromatography. If not stated otherwise, solutions of organomagnesium compounds were prepared by reacting magnesium with aryl bromides in THF and treated with I 2 Standard solutions were titrated in 0.5 M LiCl in THF and diluted with THF to the indicated concentrations. ZnBr 2 and ZnCl 2 Dry at 140° C. under high vacuum for 30 min and then dissolve in anhydrous THF.

[0060] General Rule 1 (AV1): Nickel-catalyzed chemical reactions

[0061] A solution of the nickel catalyst was prepared as follows: anhydrous nickel chloride (8.2 mg, 0.063 mmol), (EtO) 2 P(O)H (34.5 mg, 0.25 mmol) and DMAP (30.5 mg, 0.25 mmol) w...

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Abstract

According to the invention, organozink compounds of R<1>-Ar<1>-ZnY (1) type are convertible, with different functionalised aryl halides R<2>-Ar<2>-X (2) in the presence of Ni or Fe catalytic quantities in a polar solvent or a polar solvent mixture, into a polyfunctional biarylene of R<1>-Ar<1>-AR<2>-R<2> (3) type. The type (1) organic compounds are obtainable by a transmetallisation reaction of aryl-magnesium halides or lithium-aryl compounds, for example with ZnBr2.

Description

[0001] The present invention relates to a process for the formation of carbon-carbon bonds between aryl, heteroaryl, alkene or alkyne based zinc compounds and aryl, heteroaryl, alkene or alkyne compounds having a suitable leaving group. Background technique [0002] Transition metal-catalyzed cross-coupling reactions are very efficient reactions for forming C–C bonds, especially when typical S N 2 substituted Csp 2 between centers. [1] Aryl-aryl cross-couplings are one of the most important methods for forming carbon-carbon bonds. The many aromatics and especially the many heteroaromatics thus obtained are of great importance not only for the agronomic and pharmaceutical industries but also for materials science. Here, generally reliable palladium(O) catalysts are used mainly in the presence of corresponding ligands such as sterically hindered phosphines [1，2] . [3] The palladium-phosphine complex is usually used in an amount of 1-3 mole percent. However, since not only p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/04
CPCC07B37/04
Inventor 保罗·诺奇安德烈·加夫留申克里斯蒂安·夏洛特·科芬克乔治·马诺利凯克斯
Owner SALTIGO GMBH
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