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US 10,100,071 B2Granted
Heterocyclic selenamonophosphites protected on a hydroxyl group and processes for preparation thereof
AssigneeEvonik Degussa GmbH
InventorsKatrin Marie Dyballa, Robert Franke, Claudia Weilbeer, Detlef Selent, Armin Börner
Life of this patent
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Abstract
Novel heterocyclic selenamonophosphites protected on the hydroxyl group, processes for preparation thereof and the use thereof as ligand.
Claims20
A heterocyclic selenaphosphite compound having a general structure (I)
- where R2, R3, R4, R5, R6, R7, R8 and R9 are each independently selected from:
- —H, —(C1-C12)-alkyl, —O—(C1-C12)-alkyl, —(C6-C20)-aryl, —O—(C6-C20)-aryl, -halogen, —OC═O—(C1-C12)-alkyl, —S-alkyl, —S-aryl, —COO—(C1-C12)-alkyl, —CONH—(C1-C12)-alkyl, —CO—(C1-C12)-alkyl, —CO—(C6-C20)-aryl, —COOH, —SO3H, —CN, or —N[(C1-C12)-alkyl]2, where the alkyl groups are linear, branched or cyclic, where the alkyl and aryl groups are each independently unsubstituted or substituted, where each substituted —(C1-C12)-alkyl group and substituted —(C6-C20)-aryl group have at least one substituent and the at least one substituent is each independently selected from —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, fluorine, chlorine, cyano, formyl, acyl, or alkoxycarbonyl, and
- where the —R1 group is selected from:
- —(C1-C12)-alkyl, —(C1-C12)-alkyl-O—(C1-C12)-alkyl, —(C6-C20)-aryl, —(C1-C12)-alkyl-O—(C6-C20)-aryl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C6-C20)-aryl, —(C═O)—O—(C1-C12)-alkyl, -acetyl,
- where the alkyl groups are linear, branched or cyclic, where the alkyl and aryl groups mentioned are each independently unsubstituted or substituted, where substituted —(C1-C12)-alkyl groups and substituted —(C6-C20)-aryl groups have at least one substituent and the at least one substituent in each case is independently selected from —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, fluorine, chlorine, cyano, formyl, acyl, or alkoxycarbonyl,
- and the —R1* group is an organofunctional phosphite group.
3 more elements
A process for preparing at least one heterocyclic selenephosphite of the general structure (I)
- where R2, R3, R4, R5, R6, R7, R8 and R9 are each independently selected from:
- —H, —(C1-C12)-alkyl, —O—(C1-C12)-alkyl, —(C6-C20)-aryl, —O—(C6-C20)-aryl, -halogen, —OC═O—(C1-C12)-alkyl, —S-alkyl, —S-aryl, —COO—(C1-C12)-alkyl, —CONH—(C1-C12)-alkyl, —CO—(C1-C12)-alkyl, —CO—(C6-C20)-aryl, —COOH, —SO3H, —CN, or —N[(C1-C12)-alkyl]2, where the alkyl groups are linear, branched or cyclic, where the alkyl and aryl groups are each independently unsubstituted or substituted, where each substituted —(C1-C12)-alkyl group and substituted —(C6-C20)-aryl group have at least one substituent and the at least one substituent is each independently selected from —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl, and
- where the —R1 group is selected from:
- —(C1-C12)-alkyl, —(C1-C12)-alkyl-O—(C1-C12)-alkyl, —(C6-C20)-aryl, —(C1-C12)-alkyl-O—(C6-C20)-aryl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C6-C20)-aryl, —C═O—O—(C1-C12)-alkyl, or acetyl, where the alkyl groups are linear, branched or cyclic, where the alkyl and aryl groups mentioned are each independently unsubstituted or substituted, where substituted —(C1-C12)-alkyl groups and substituted —(C6-C20)-aryl groups have at least one substituent and the at least one substituent in each case is independently selected from —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl,
- and the —R1* group is an organofunctional phosphite group.
- comprising at least the process step of
- (i) reacting a selenodiaryl of the general structure (IX)
- where R2, R3, R4, R5, R6, R7, R8 and R9 are each independently selected from:
- —H, —(C1-C12)-alkyl, —O—(C1-C12)-alkyl, —(C6-C20)-aryl, —O—(C6-C20)-aryl, -halogen, —OC═O—(C1-C12)-alkyl, —S-alkyl, —S-aryl, —COO—(C1-C12)-alkyl, —CONH—(C1-C12)-alkyl, —CO—(C1-C12)-alkyl, —CO—(C6-C20)-aryl, —COOH, —SO3H, —CN, or —N[(C1-C12)-alkyl]2, where the alkyl groups are linear, branched or cyclic, where the alkyl and aryl groups are each independently unsubstituted or substituted, where each subtituted —(C1-C12)-alkyl group and substituted —(C6-C20)-aryl group have at least one substituent and the at least one substituent is each independently selected from —(C3-C12)-cycloalkyl, —(C3-C12)—heterocycloalkyl, —(C6-C20)-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl,
- and —R1 group is selected from:
- —(C1-C12)-alkyl, —(C1-C12)-alkyl-O—(C1-C12)-alkyl, —(C6-C20)-aryl, —(C1-C12)-alkyl-O—(C6-C20)-aryl, —(C6-C20)-aryl-O—(C1-C12)-alkyl, —(C6-C20)-aryl-O—(C6-C20)-aryl, —C═O—O—(C1-C12)-alkyl, or acetyl, where the alkyl groups are linear, branched or cyclic, where the alkyl and aryl groups mentioned are each independently unsubstituted or substituted, where substituted —(C1-C12)-alkyl groups and substituted —(C6-C20)-aryl groups have at least one substituent and the at least one substituent in each case is independently selected from —(C3-C12)-cycloalkyl, —(C3-C12)-heterocycloalkyl, —(C6-C20)-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl,
- (ii) with at least one halophosphite compound R1*Hal where Hal is selected from fluorine, chlorine, bromine, iodine, and where —R1* is an organofunctional bivalent phosphite group,
- (iii) and obtaining at least one selenaphosphite of the general structure (I).
10 more elements
The method of claim14, wherein (i) the reaction is effected in the temperature range from −15 to 30° C.
Dependencies are inferred from the claim text.