Tetradentate ligand, and production method therefor, synthetic intermediate thereof, and transition metal complex thereof

Patent metadata

Field	Value
Publication number	US-10550141-B2
Application number	US-201716089730-A
Country	US
Kind code	B2
Filing date	Mar 30, 2017
Priority date	Mar 30, 2016
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

The present invention relates to: a compound as a ligand in a variety of catalytic organic synthetic reactions; a method for producing the compound; a synthetic intermediate of the compound; and a transition metal complex which has the compound as a ligand. The compound includes a compound represented by the following general formula (1 A ):

First claim

The invention claimed is:

1. A compound represented by the following formula (1 A ):

wherein the solid lines represent a single bonds and the double lines represent double bonds, C represents a carbon atom, H represents a hydrogen atom and N represents a nitrogen atom, each of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , and R 15 independently represents a group selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, and an aralkyl group, and G represents a group selected from the group consisting of a monovalent group represented by the following formula (G P ) and a monovalent group represented by the following formula (G S ):

wherein the solid lines represent a single bonds, a dotted line represents a coordinate bond and a solid line intersected by a wavy line represents a bond to an adjacent atom, P represents a phosphorus atom, L represents a lone electron pair or a boron trihydride, each of R 1 and R 2 independently represents a group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heteroaryl group, and an aralkyl group, and R 1 and R 2 may combine with each other to form a phosphorus atom-containing ring; and

wherein a solid line represents a single bond and a solid line intersected by a wavy line represents a bond to an adjacent atom, S represents a sulfur atom, and R 3 represents a group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heteroaryl group, and an aralkyl group; and an alkenyl group in R 1 to R 3 , an aryl group in R 1 to R 3 , a heteroaryl group in R 1 to R 3 , an aralkyl group in R 1 to R 3 , and a phosphorus atom-containing ring formed by combining R 1 with R 2 each other may be substituted by a substituent selected from the group consisting of an alkyl group, a cycloalkyl group, a halogenoalkyl group, an aryl group, an aralkyl group, an alkoxy group, a silyl group, and a halogeno group.

2. The compound according to claim 1 , wherein all of the R 5 to R 15 are hydrogen atoms.

3. The compound according to claim 1 , which is an optically active substance.

4. A method for producing the compound according to claim 1 , comprising subjecting a compound represented by the following formula (2 A ) to a reaction with a compound represented by the following formula (3):

wherein the solid lines represent single bonds and double lines represent double bonds, C represents a carbon atom, N represents a nitrogen atom, O represents an oxygen atom, and each of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , and R 15 independently represents a group selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, and an aralkyl group; and

wherein the solid line represents a single bond, H represents a hydrogen atom, and G represents the same group as G defined in claim 1 .

5. A compound represented by the following formula (2 A ):

wherein the solid lines represent single bonds and double lines represent double bonds, C represents a carbon atom, N represents a nitrogen atom, O represents an oxygen atom, and each of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , and R 15 independently represents a group selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, and an aralkyl group.

6. The compound according to claim 5 , wherein all of the R 5 to R 15 are hydrogen atoms.

7. The compound according to claim 5 , which is an optically active substance.

8. A ruthenium complex comprising the compound according to claim 1 as a ligand.

9. An iron complex comprising the compound according to claim 1 as a ligand.

Assignees

• Takasago Perfumery Co Ltd

Inventors

• Nakayama Yuji
• Yokoyama Naota

Classifications

• C07D263/38

  attached in position 2 · CPC title

• B01J2531/0216

  Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp · CPC title

• B01J2531/842

  Iron · CPC title

• B01J2531/822

  Rhodium · CPC title

• B01J31/22

  Organic complexes · CPC title