Nitrogen-containing ligands
OwnerWilliam Hems, Weiping Chen +1inventors
InventorsWilliam Hems, Weiping Chen, Jianliang Xiao
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Abstract
An immobilised nitrogen-containing ligand is described comprising the reaction product of a compound of formula (I) wherein R5, R6, R7 and R8 are independently hydrogen, a saturated or unsaturated C1-C10 alkyl group, an aryl group, a urethane group, a sulphonyl group or form an imine group, R1, R2, R3, and R4 are independently hydrogen, a saturated or unsaturated C1-C10 alkyl group or an aryl group and at least one of R1, R2, R3 and R4 is functionalised with a functional group, and a solid support having a site capable of reacting with said functional group. The nitrogen-containing ligand is useful for preparing immobilised catalysts for performing e.g. asymmetric catalysis.
Claims17
1-18. (canceled)
A ligand of formula (I)
- wherein R1 and R3 are H;
- R5, R6, R7 and R8 are selected from the group consisting of hydrogen and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, imide, and reaction products of any of these with a polyethylene glycol.
A ligand of formula (II)
- wherein R1 and R3 are H;
- R5 and R7 are selected from the group consisting of hydrogen, saturated or unsaturated C1-C10 alkyl, aryl, urethane, and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, imide, and reaction products of any of these with a polyethylene glycol.
An immobilized nitrogen-containing ligand comprising a reaction product of a ligand of formula (I)
- wherein R1 and R3 are H;
- R5, R6, R7 and R8 are selected from the group consisting of hydrogen and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, and imide;
- with a solid support having a site capable of reacting with said substituent.
An immobilized nitrogen-containing ligand comprising a reaction product of a ligand of formula (II)
- wherein R1 and R3 are H;
- R5 and R7 are selected from the group consisting of hydrogen, saturated or unsaturated C1-C10 alkyl, aryl, urethane, and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, and imide;
- with a solid support having a site capable of reacting with said substituent.
A method for preparing a ligand of formula (I)
- wherein R1 and R3 are H;
- R5, R6, R7 and R8 are selected from the group consisting of hydrogen and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, and imide;
- comprising the steps of:
- (a) performing a benzoin condensation on a functionalised benzaldehyde to give a functionalised benzoin;
- (b) reducing the functionalised benzoin by asymmetric hydrogen transfer hydrogenation using a Ru catalyst to give a functionalised hydrobenzoin;
- and
- (c) transforming the functionalised hydrobenzoin via a diazide into a functionalised 1,2-diarylamine.
A method for preparing a ligand of formula (II)
- wherein R1 and R3 are H;
- R5 and R7 are selected from the group consisting of hydrogen, saturated or unsaturated C1-C10 alkyl, aryl, urethane, and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, and imide;
- comprising the steps of:
- (a) performing a benzoin condensation on a functionalised benzaldehyde to give a functionalised benzoin;
- (b) reducing the functionalised benzoin by asymmetric hydrogen transfer hydrogenation using a Ru catalyst to give a functionalised hydrobenzoin;
- and
- (c) transforming the functionalised hydrobenzoin via a diazide into a functionalised 1,2-diarylamine.
A method for preparing an immobilized nitrogen-containing ligand, the method comprising contacting a ligand of formula (I)
- wherein R1and R3 are H;
- R5, R6, R7 and R8 are selected from the group consisting of hydrogen and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, and imide;
- with a solid support having a site capable of reacting with said substituent to form the immobilised nitrogen-containing ligand.
A method for preparing an immobilized nitrogen-containing ligand, the method comprising contacting a ligand of formula (II)
- wherein R1 and R3 are H;
- R5 and R7 are selected from the group consisting of hydrogen, saturated or unsaturated C1-C10 alkyl, aryl, urethane, and sulfonyl, provided that only one of these may be sulfonyl;
- and wherein R2 and R4 are aryl groups each comprising a substituent selected from the group consisting of Cl, Br, F, I, hydroxyl, alkoxy, carbonyl, carboxyl, anhydride, carbene, methacryl, epoxide, vinyl, nitrile, mercapto, amine, imine, amide, and imide;
- with a solid support having a site capable of reacting with said substituent to form the immobilised nitrogen-containing ligand.
Dependencies are inferred from the claim text.