# US 5,344,970 A · Hydrogenation of aromatic-substituted olefins using organometallic catalyst

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- Number: US 5,344,970 A
- Document ID: US5344970A
- Status: Granted
- Kind: A
- Application number: 08/173,795
- Filed: 1993-12-22
- Granted: 1994-09-06
- Earliest claimed: 1990-12-10
- Assignees: Albemarle Corporation
- Inventors: Charles H. Kolich
- Web page: https://patentgrep.com/patent/US5344970A

## CPC

- C07F 15/0053: {without a metal-carbon linkage}
- B01J 31/185: {Phosphites ((RO)3P) , their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof}
- C07C 51/36: by hydrogenation of carbon-to-carbon unsaturated bonds
- B01J 2231/645: of C=C or C-C triple bonds
- B01J 2531/0266: Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
- B01J 2531/821: Ruthenium
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A ruthenium-phosphite complex having the formula ##STR1## wherein a is from 1 to 3; b is 1 or 2; c is from 0 to 3; and R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR2## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl. This complex can be used to effect the reduction of unsaturated organic compounds or, when comprised of ligands having optical activity, can be used as the catalyst for effecting the asymmetric reduction of unsaturated organic compounds.

## Claims

### Claim 1

A process for the enantioselective hydrogenation of an aromatic-substituted olefin of the formula ##STR10## where Z is ##STR11## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex of the formula ##STR12## wherein a is from 1 to 3, b is 1 or 2, c is from 0 to 3; R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR13## where R.sub.1, R.sub.2 and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; and R.sub.4 taken together with the nitrogen atom is a straight or branched chain alkyl of 1 to 20 carbon atoms; in the presence of gaseous hydrogen for a time and at a temperature sufficient to effect enantiomonic reduction of at least a portion of the double bond of said olefin.

### Claim 2 (depends on 1)

The process according to claim 1 where R.sub.1 is methyl or ethyl.

### Claim 3 (depends on 1)

The process according to claim 1 where R.sub.2 and R.sub.3 are the same and are isopropyl or tertiary butyl.

### Claim 4 (depends on 1)

The process according to claim 1 where R is hydrogen.