PROCESS FOR HYDROGENATING KETONES IN THE PRESENCE OF RU(II) CATALYSTS

1 . A process for hydrogenating a substrate comprising a carbon-heteroatom double bond, the process comprising the step of reacting the substrate with hydrogen gas in the presence of a hydrogenation catalyst, wherein the hydrogenation catalyst is a complex of formula (I):

wherein,

R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, optionally substituted straight, branched or cyclic C 1-20 alkyl, optionally substituted straight, branched or cyclic C 1-20 alkoxy, optionally substituted C 6-20 aryl, optionally substituted C 6-20 aryloxy, —OH, —CN, —NR 20 R 21 , —COOH, COOR 20 , —CONH 2 , —CONR 20 R 21 and —CF 3 , wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN, —NR 30 R 31 , —COOR 30 , —CONR 30 R 31 and —CF 3 ;

R 1 and R 2 , R 2 and R 3 , R 3 and R 4 or R 4 and R 5 together form an aromatic ring composed of 6 to 10 carbon atoms which is optionally substituted with one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 ;

R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen, optionally substituted straight, branched or cyclic C 1-20 alkyl, optionally substituted straight, branched or cyclic C 1-20 alkoxy, optionally substituted C 6-20 aryl and optionally substituted C 6-20 aryloxy wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 , or

R 6 and R 7 together with the carbon atom to which they are bound and/or R 8 and R 9 together with the carbon atom to which they are bound form an optionally substituted C 3-20 cycloalkyl or an optionally substituted C 2-20 cycloalkoxy, wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 , or

one of R 6 and R 7 and one of R 8 and R 9 together form an optionally substituted C 5-10 cycloalkyl or an optionally substituted C 5-10 cycloalkoxy, wherein the substituents are independently selected from the group consisting of one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 , or

R 10 is an optionally substituted straight, branched or cyclic C 1-10 alkyl, an optionally substituted C 6-10 aryl or —NR 11 R 12 wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-10 alkyl, straight, branched or cyclic C 1-10 alkoxy, C 6-10 aryl, C 6-10 aryloxy, -Hal, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 ;

R 11 and R 12 are independently selected from the group consisting of hydrogen, optionally substituted straight, branched or cyclic C 1-10 alkyl and optionally substituted C 6-10 aryl, wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-10 alkyl groups, straight, branched or cyclic C 1-10 alkoxy, C 6-10 aryl, C 6-10 aryloxy, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 , or

R 11 and R 12 together with the nitrogen atom to which they are bound form an optionally substituted C 2-10 cycloalkyl-amino group wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-10 alkyl, straight, branched or cyclic C 1-10 alkoxy, C 6-10 aryl, C 6-10 aryloxy, —OH, —CN, —NR 20 R 21 , —COOR 20 , —CONR 20 R 21 and —CF 3 ;

R 20 and R 21 are independently selected from the group consisting of hydrogen, optionally substituted straight, branched or cyclic C 1-20 alkyl, optionally substituted straight, branched or cyclic C 1-20 alkoxy, optionally substituted C 6-20 aryl, optionally substituted C 6-20 aryloxy, —OH, —CN, —NR 30 R 31 , —COOR 30 , —CONR 30 R 31 and —CF 3 , wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN and —CF 3 ;

R 30 and R 31 are independently selected from the group consisting of hydrogen, optionally substituted straight, branched or cyclic C 1-20 alkyl, optionally substituted straight, branched or cyclic C 1-20 alkoxy, optionally substituted C 6-20 aryl, optionally substituted C 6-20 aryloxy, —OH, —CN and —CF 3 , wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN and —CF 3 ;

A is an optionally substituted straight- or branched-chain C 2-5 alkyl wherein the substituents are selected from the group consisting of one or more straight, branched or cyclic C 1-10 alkyl, straight, branched or cyclic C 1-10 alkoxy, C 6-10 aryl and C 6-10 aryloxy, or

A is a group of formula (II):

wherein p is an integer selected from 1, 2, 3 or 4;

each R 40 is independently selected from the group consisting of straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN or —CF 3 ;

q and r are independently integers selected from 0, 1, 2 or 3 wherein q+r=1, 2 or 3;

each R 41 is independently selected from the group consisting of hydrogen, straight, branched or cyclic C 1-20 alkyl, straight, branched or cyclic C 1-20 alkoxy, C 6-20 aryl, C 6-20 aryloxy, —OH, —CN and —CF 3 ; and

Hal is a halogen.

2 . A process according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, straight-chain C 1-10 alkyl and branched-chain C 1-10 alkyl.

3 . A process according to claim 2 , wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl and t-butyl.

4 . A process according to claim 3 , wherein R 1 , R 2 , R 3 , R 4 and R 5 are each hydrogen.

5 . A process according to claim 1 , wherein R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen and optionally substituted C 6-10 aryl.

6 . A process according to claim 5 , wherein R 6 , R 7 , R 8 and R 9 are each independently selected from the group consisting of hydrogen and phenyl.

7 . A process according to claim 6 , wherein one of R 6 and R 7 is phenyl and the other of R 6 and R 7 is hydrogen.

8 . A process according to claim 6 , wherein one of R 8 and R 9 is phenyl and the other of R 8 and R 9 is hydrogen.

9 . A process according to claim 6 , wherein R 6 , R 7 , R 8 and R 9 are hydrogen.

10 . A process according to claim 1 , wherein R 10 is methyl or a tolyl group.

11 . A process according to claim 1 , wherein A is —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 — or —(CH 2 ) 5 —.

12 . A process according to claim 1 , wherein Hal is selected from the group consisting of chlorine, bromine and iodine.

13 . A process according to claim 1 , wherein the substrate to be hydrogenated is a carbonyl or iminyl.

14 . A process according to claim 1 , further comprising a solvent.

15 . A process according to claim 14 , wherein the solvent comprises an alcohol.

16 . A process according to claim 1 , further comprising a silver salt.

17 . A process according to claim 1 , further comprising a fluorinated sulfonic acid.