Tetradentate ferrocene ligands and their use

Details Tetradentate ferrocene ligands and their use Tetradentate ferrocene ligands and their use

C - Chemistry, Metallurgy

07

F

C07F 15/02 (2006.01)

Patent

CA 2572650

Compounds of the formula (I) in the form of racemates, mixtures of diastereomers or pure diastereomers, where RO and Roo are each, independently of one another, hydrogen, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C14-aryl or C3- C12-heteroaryl having heteroatoms selected from the group consisting of O, S and N, which are unsubstituted or substituted by C1-C6-alkyl, C1-C6-alkoxy, C5- C8-cyclo~alkyl, C5-C8-cycloalkoxy, phenyl, C1-C6-alkylphenyl, C1-C6- alkoxyphenyl, C3-C8-heteroaryl, F or trifluoromethyl; the radicals R1 are each, independently of one another, a hydrogen atom, a halogen atom or a substituent bound to the cyclopentadienyl rings via a C atom, S atom, Si atom, a P(O) or P(S) group; R2 and R02 are each, independently of one another, a hydrogen atom, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C14-aryl or C3-C12- heteroaryl having heteroatoms selected from the group consisting of O, S and N, which are unsubstituted or substituted by C1-C6-alkyl, C1-C6~-alkoxy, C5-C8- cycloalkyl, C5-C8-cycloalkoxy, phenyl, C1-C6-alkylphenyl, C1-C6-alkoxyphenyl, C3-C8-heteroaryl, F or trifluoromethyl; the two indices m are each, independently of one another, 1, 2 or 3; n is 0 or 1; X1 is a secondary phosphine group or a cyclic phosphonite group, and X2 and X3 are each, independently of one another, a secondary phosphine group. The compounds of the formula (I) are valuable ligands for enantioselective catalysts for the hydrogenation of prochiral, unsaturated compounds.

L'invention concerne les composés de formule (I) se présentant sous la forme de racémates, de mélange de diastéréomères ou de diastéréomères purs. Dans la formule (I), R0 et R00sont chacun indépendamment hydrogène, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C14-aryl ou C3-C12-hétéroaryl portant des hétéroatomes choisis dans le groupe de O, S et N, non substitués ou substitués par C1-C6-alkyl, C1-C6-alkoxy, C5-C8-cycloalkyl, C5-C8-cycloalkoxy, phényl, C1-C6-alkylphényl, C1-C6-alkoxyphényl, C3-C8-hétéroaryl, F ou trifluorométhyl; les radicaux R1 sont chacun indépendamment un atome d'hydrogène, un atome d'halogène ou un substituant lié aux cycles cyclopentadiényl par un atome de C, S ou Si, ou un groupe P(O) ou P(S); R2 et R02 sont chacun indépendamment un atome d'hydrogème, C1-C20-alkyl, C3-C8-cycloalkyl, C6-C14-aryl ou C3-C12-hétéroaryl portant des hétéroatomes choisis dans le groupe de O, S et N, non substitués ou substitués par C1-C6-alkyl, C1-C6-alkoxy, C5-C8-cycloalkyl, C5-C8-cycloalkoxy, phényl, C1-C6-alkylphényl, C1-C6-alkoxyphényl, C3-C8-hétéroaryl, F ou trifluorométhyl; les deux indices m sont chacun indépendamment 1, 2,ou 3; X1 est un groupe phosphine secondaire ou un groupe phosphonite cyclique; et X2 et X3 sont chacun indépendamment un groupe phosphine secondaire. Les composés de la formule (I) sont des ligands efficaces de catalyseurs énantiosélectifs pour l'hydrogénation de composés prochiraux insaturés.

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