Perfluoro-n-alkylsulfonic acid derivatives
AssigneeMerck Patent GmbH
InventorsAndreas Wachtler, Karl-Heinz Derwenskus, Andreas Meudt
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Abstract
Described are bis(perfluoro-n-alkane-sulfonate) compounds, methods for preparing these compounds and use of these compounds, for example as starting materials for the synthesis of chiral and phosphine ligands for transition metal catalysts.
Drawings
Claims10
Bis(perfluoro-n-alkanesulfonates) of the formula I:
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- where
- n is 3, 4, 5, 6, 7, 8 or 9,
- A is
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- B is —(CHR)4—,
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- where nonadjacent groups ═CR— may be replaced by ═N—, and —CHR— may be replaced by —NR—, —O— or —S— and
- R is alkyl or alkoxy having from 1 to 12 carbon atoms, halogen, —CN, —CF3, —OCF3 or unsubstituted phenyl or phenyl which is monosubstituted or polysubstituted by alkyl or alkoxy having from 1 to 12 carbon atoms, halogen or —CN, where if more than one R is present the substituents R may be identical or different.
Compounds of the formulae I1, I2, I3, I7 and I8:
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- where n is as defined above and R1 is alkyl or alkoxy having from 1 to 3 carbon atoms, F, Br, CF3 or CN.
Use of the bis(perfluoro-n-alkanesulfonates) of the formula I for preparing diphosphines of the formula III:
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- where A and B are as defined above and
- R2,R3 are phenyl, 4-methylphenyl, 3-methylphenyl, 2-methylphenyl, 3,5-dimethylphenyl, 3,5-di-tert-butylphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 3,5-dimethoxyphenyl, cyclohexyl or cyclopentyl.
Process for preparing the compounds of the formula III, characterized in that the compounds of the formula I are reacted in the presence of a transition metal catalyst and a base either with phosphines of the formula IV
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- or with zinc and phosphines of the formula V
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- where R2 and R3 are as defined above.
Dependencies are inferred from the claim text.