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US 10,544,179 B2Granted
Organic compounds
AssigneeGivaudan SA
InventorsRoger Wilhelm Geisser, Jürg Daniel Oetiker, Fridtjof Schröder
Life of this patent
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Abstract
A process for the hydrogenation of a substrate comprising a carbon heteroatom double bond in the presence of a transition metal complex comprising a tridentate or bisdentate-ligand containing a nitrogen, sulphur and phosphorus atom, of which at least the N- and P- and optionally also the S-atom coordinates with the transition metal.
Claims8
A transition metal complex according to the formula:
- MX2[SNP]Y
- wherein M is a group VIII transition metal and SNP represents a tridentate or bisdentate ligand containing a nitrogen, sulphur and phosphorus atom, of which at least the N- and P- and optionally also the S-atom coordinates with the transition metal, each X is independently selected from a halide, hydroxyl, alkoxy, acyloxy and amido;
- and each Y is independently selected from a monodentate phosphine, a carbon monoxide (CO) ligand, a nitrosyl group and a RCN group, wherein R is alkyl or aryl,
- wherein the tridentate or bisdentate ligand is represented by the formula
- wherein
- R1 and R2 are independently selected from H, or C1 to C20 alkyl and aryl, or R1 and R2 are connected such that together with the sulphur and carbon atoms to which they are attached, they form a heteroaliphatic or heteroaromatic ring;
- R3 through R7 are independently selected from H;
- a C1 to C20 linear or branched alkyl group or alkenyl group;
- a C3 to C8 cyclic alkyl group;
- and a C5 to C10 aryl group;
- or R2 and R3;
- R3 and R4;
- or R2 and R4, together with the carbon atoms to which they are attached form a 5- or 6-membered aliphatic ring, which is optionally unsaturated;
- and/or R5 and R6;
- R5 and R7;
- or R6 and R7, together with the carbon atoms to which they are attached form a 5- or 6- membered aliphatic ring, which is optionally unsaturated;
- R8 and R9 independently are selected from H;
- a C1 to C20 linear or branched alkyl group or alkenyl group;
- a C3 to C8 cyclic alkyl group;
- and a C5 to C10 aryl or heteroaryl group;
- a and b are independently 0, 1 or 2;
- n is 0 or 1;
- and
- represents a single or a double bond, provided that when R2 is H or C4 to C20 alkyl represents a single bond;
- and when n is 1 each N represents a carbon-nitrogen single bond;
- whereas when n is 0, one N is a carbon-nitrogen single bond and the other N is a carbon-nitrogen double bond.
23 more elements
A tridentate or bisdentate ligand L presented by the formula
- wherein
- R1 and R2 are independently selected from H, and C1 to C20 alkyl or aryl, or R1 and R2 are connected such that together with the sulphur and carbon atoms to which they are attached, they form a heteroaromatic or heteroaliphatic ring, and wherein said heteroaromatic ring is not a 5-membered heterocycle containing both S and N atoms;
- R3 through R7 are independently selected from H;
- a C1 to C20 linear or branched alkyl group or alkenyl group;
- a C3 to C8 cyclic alkyl group;
- and a C5 to C10 aryl group;
- or R2 and R3;
- R3 and R4;
- or R2 and R4, together with the carbon atoms to which they are attached form a 5- or 6-membered aliphatic ring, which is optionally unsaturated;
- and/or R5 and R6;
- R5 and R7;
- or R6 and R7, together with the carbon atoms to which they are attached form a 5- or 6-membered aliphatic ring, which is optionally unsaturated;
- R8 and R9 independently are selected from H;
- a C1 to C20 linear or branched alkyl group or alkenyl group;
- a C3 to C8 cyclic alkyl group;
- and a C5 to C10 aryl or heteroaryl group;
- a and b are independently 0, 1 or 2;
- n is 0 or 1;
- and
- represents a single or a double bond, provided that when R2 is H or C4 to C20 alkyl, represents a single bond;
- and when n is 1 each N represents a carbon-nitrogen single bond;
- whereas when n is 0, one N is a carbon-nitrogen single bond and the other N is a carbon-nitrogen double bond;
- with the proviso that the ligand L is not
- wherein the tridentate or bisdentate ligand is represented by the formula selected from the group consisting of
- wherein
- R10 is a moiety selected from C1-10 alkyl, aryl, heteroaryl, alkenyl, nitrile and halide, and
- m is 0,1,2 or 3.
24 more elements
Dependencies are inferred from the claim text.