Method for producing compound

Patent metadata

Field	Value
Publication number	US-9982087-B2
Application number	US-201414912946-A
Country	US
Kind code	B2
Filing date	Jul 31, 2014
Priority date	Aug 22, 2013
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

A method is provided for producing a compound, including a step of mixing a compound (1) having one or two leaving groups, a compound (2) having one or two boron atom-containing leaving groups, an organic base (P), and at least one selected from a phase transfer catalyst and an organic base (Q) larger in the number of carbon atoms than the above-mentioned organic base in the presence of a transition metal catalyst. The method thereby performs a coupling reaction between the above-mentioned compound (1) and the above-mentioned compound (2).

First claim

The invention claimed is:

1. A method for producing a compound, the method comprising mixing a first compound having two leaving groups, a second compound having two boron atom-containing leaving groups, an organic base, and a phase transfer catalyst having a larger number of carbon atoms than the organic base in the presence of a divalent palladium catalyst, such that the method performs a coupling reaction between the first compound and the second compound.

2. The method for producing a compound according to claim 1 , wherein the leaving groups of the first compound are selected from halogen atoms, diazonio groups or groups represented by —O—S(═O) 2 R C1 , wherein R C1 represents optionally substituted alkyl or aryl groups.

3. The method for producing a compound according to claim 1 , wherein the phase transfer catalyst is an ammonium compound.

4. The method for producing a compound according to claim 3 , wherein the ammonium compound has 16 to 60 carbon atoms.

5. The method for producing a compound according to claim 1 , wherein the phase transfer catalyst is at least one selected from the group consisting of (C 4 H 9 ) 4 NF, (C 4 H 9 ) 4 NCl, (C 4 H 9 ) 4 NBr, (C 4 H 9 ) 4 NI, (C 5 H 11 ) 4 NCl, (C 5 H 11 ) 4 NBr, (C 5 H 11 ) 4 NI, (C 16 H 33 )(CH 3 ) 3 NCl, (C 8 H 17 ) 3 (CH 3 )NCl, (C 8 H 17 ) 2 (C 10 H 21 )(CH 3 )NCl, (C 8 H 17 )(C 10 H 2 O 2 (CH 3 )NCl, (C 10 H 21 ) 3 (CH 3 )NCl, and (C 8 H 17 ) 4 NBr.

6. The method for producing a compound according to claim 1 , wherein the organic base is an organic base having 4 to 15 carbon atoms.

7. The method for producing a compound according to claim 1 , wherein the organic base is an ammonium hydroxide compound having 4 to 15 carbon atoms.

8. A method for producing a compound, the method comprising mixing a first compound having two leaving groups, a second compound having two boron atom-containing leaving groups, a first organic base, and a second organic base larger in number of carbon atoms than the first organic base in the presence of a divalent palladium catalyst, such that the method performs a coupling reaction between the first compound and the second compound, and wherein the second organic base is an ammonium hydroxide compound having 16 to 60 carbon atoms.

9. The method for producing a compound according to claim 1 , wherein the first compound is a compound represented by the formula (A) and the second compound is a compound represented by the formula (B):

wherein R 1 and R 2 each independently represent an organic group,
X 1 represents Cl, Br, I or —O—S(═O) 2 R C1 , wherein R C1 represents an alkyl group or an aryl group and these groups optionally have a substituent,
X 2 represents B(R C2 ) 2 , B(ORC C2 ) 2 or BF 3 T, wherein R C2 represents a hydrogen atom, an alkyl group or an aryl group and these groups optionally have a substituent, and the R C2 s may be the same or different and they may be combined together to form a ring together with the boron atom to which they are attached or together with the oxygen atoms to which they are attached and the boron atom to which the oxygen atoms are attached, and T represents Li, Na, K, Rb or Cs, and
n and m each represent 2.

10. The method for producing a compound according to claim 9 , wherein R 1 and R 2 each independently represent an organic group having 1 to 60 carbon atoms.

11. The method for producing a compound according to claim 10 , wherein the organic group is an aromatic group having 6 to 20 carbon atoms and optionally having a substituent.

12. The method for producing a compound according to claim 1 , wherein the divalent palladium catalyst is dichlorobis(triphenylphosphine)palladium, dichlorobis[tris(2-methoxyphenyl)phosphine]palladium, dichlorobis[dicyclopentyl(2-methoxyphenyl)phosphine]palladium, dichlorobis[dicyclopentyl(2,6-dimethoxyphenyl)phosphine]palladium or bis[di-tert-butyl(3,5-di-tert-butylphenyl)phosphine]dichloropalladium.

Assignees

• Sumitomo Chemical Co

Inventors

• Kashima Ken
• Hida Noriyuki

Classifications

• C08G2261/411

  Suzuki reactions · CPC title

• C07C2531/22

  Organic complexes · CPC title

• C08G61/122

  derived from five- or six-membered heterocyclic compounds, other than imides · CPC title

• C08G2261/1426

  containing carboxy groups (COOH) and/or -C(=O)O-moieties · CPC title

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title