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Bipyridyl compound

Foreign code F180009351
File No. E112P05US2
Posted date Apr 17, 2018
Country United States of America
Application number 201715819180
Gazette No. 20180072672
Gazette No. 10280142
Date of filing Nov 21, 2017
Gazette Date Mar 15, 2018
Gazette Date May 7, 2019
International application number JP2015052450
International publication number WO2015115519
Date of international filing Jan 29, 2015
Date of international publication Aug 6, 2015
Priority data
  • P2014-015211 (Jan 30, 2014) JP
  • 2015JP52450 (Jan 29, 2015) WO
  • 201615114347 (Jul 26, 2016) US
Title Bipyridyl compound
Abstract There are provided a compound capable of being a novel ligand allowing regioselective borylation to be performed in the aromatic borylation reaction, and a catalyst using the same compound. There is provided a bipyridyl compound represented by a general formula (1): (wherein A represents a single bond, a vinylene group or an ethynylene group; - - X represents an oxygen atom or a sulfur atom; - n pieces of R1 may be the same or different, and R1 represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted amino group, a cyano group, a nitro group, or an alkoxycarbonyl group, or two adjacent R1 may form a saturated or unsaturated ring structure optionally containing a hetero atom together with the carbon atoms bonded to the two R1; - R2 represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group; and - n represents a number of 1 to 4).
Outline of related art and contending technology BACKGROUND OF THE INVENTION
The Suzuki-Miyaura reaction performing a cross coupling between an organic halogen compound and an organic boron compound is an important method for carbon-carbon bond formation reaction and is widely applied. The organic boron compound used in this reaction is stable against water or air, and the product of the reaction is a boric acid salt to be thereby low in toxicity and has an advantage of being easily separable from the target product by washing with water.
For the purpose of synthesizing a wide range of compounds by using the Suzuki-Miyaura reaction, it is important to produce compounds each having a boron atom bonded to a specific position in an aromatic compound. In this connection, catalysts such as rhodium catalysts, iridium catalysts and rhenium catalysts are known as the catalysts for the aromatic borylation reactions allowing boron atoms to be bonded to aromatic compounds. In these catalysts, bipyridyl compounds, ethylenediamine compounds, phenanthroline compounds, cyclopentadienyl compounds and the like are used as ligands (Non Patent Literature 1 to Non Patent Literature 9).
Scope of claims [claim1]
1. A bipyridyl compound represented by a formula (1):
wherein A represents a single bond at an ortho-position relative to the uredio group;
X represents an oxygen atom;
n pieces of R1 may be the same or different, and
R1 represents a hydrogen atom, a halogen atom, a C1-10 alkyl group, a C2-10 alkenyl group, a C3-7 cycloalkvl group, a C6-10 aryl group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted amino group, a cyano group, a nitro group, or an alkoxycarbonyl group, or two adjacent R1 may form a saturated or unsaturated ring structure optionally containing a hetero atom together with the carbon atoms bonded to the two R1;
R2 represents a hydrogen atom, an unsubstituted C1-16 hydrocarbon group, a C1-16 hydrocarbon group substituted with a halogen, a C1-6 alkoxy group, a C1-6 alkyl group, or a halgeno-C1-6 alkyl group, an optionally substituted alkoxy group, or an optionally substituted aryloxy group; and
n represents a number of 1 to 4,
wherein the optional substitution on the hydrocarbon group of R1 is 1 to 3 halogen atoms, a cyano group, a nitro group, a halogeno C1-6 alkyl group or a C1-6 alkoxy group,
wherein the optional substitution on the alkoxy group and the aryloxy group of R1 is 1 to 3 halogen atoms, a cyano group, a nitro aroup, a halogeno C1-6 alkyl group or a C1-6 alkoxy group,
wherein the optional substitution on the amino group of R1 is a C1-6 alkyl group or a halogeno C1-6 alkyl group,
wherein the optional substitution on the hydrocarbon group of R2 is 1 to 3 halogen atoms, a cyano group, a nitro group, a halogeno C1-6 alkyl group or a C1-6 alkoxy group,
wherein the optional substitution on the alkoxy group and the aryloxy group of R2 is 1 to 3 halogen atoms, a cyano group, a nitro group, a halogeno C1-6 alkyl group or a C1-6 alkoxy group.

[claim2]
2. The bipyridyl compound according to claim 1, wherein R1 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a C1-6 alkylamino group, a di(C1-6 alkyl)amino group or a C1-10 alkoxycarbonyl group.

[claim3]
3. The bipyridyl compound according to claim 1, wherein R2 is a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, an optionally substituted alkenyl group having 2 to 10 carbon atoms, an optionally substituted cycloalkyl group having 3 to 7 carbon atoms, an optionally substituted aryl group having 6 to 10 carbon atoms, an optionally substituted alkoxy group having 1 to 10 carbon atoms or an optionally substituted aryloxy group having 6 to 10 carbon atoms.

[claim4]
4. The bipyridyl compound according to claim 1, wherein when R2 is a substituted non-heterocyclic group, the substitution is selected from the group consisting of 1 to 3 halogen atoms, a cyano group, a halogeno C1-6 alkyl group and a C1-6 alkoxy group.

[claim5]
5. The bipyridyl compound according to claim 1, which is 1-(2-([2,2′-Bipyridin]-5-yl)phenyl-3-(4-methoxyphenyl)urea.

[claim6]
6. The bipyridyl compound according to claim 1, which is 1-(2-([2,2′-Bipyridin]-5-yl)pheryl)-3-cyclohexylthiourea.

[claim7]
7. The bipyridyl compound according to claim 1, which is 1-(2-([2,2′-Bipyridin]-5-ylethynyl)phenyl)-3-phenylurea.

[claim8]
8. The bipyridyl compound according to claim 1, wherein R1 is a hydrogen atom.

[claim9]
9. The bipyridyl compound according to claim 1, wherein A represents a single bond or an ethynylene group.

[claim10]
10. The bipyridyl compound according to claim 1, wherein R1 represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted amino group, a cyano group, a nitro group, or an alkoxycarbonyl group.

[claim11]
11. The bipyridyl compound according to claim 9, wherein R1 represents a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted aryloxy group, an optionally substituted amino group, a cyano group, a nitro group, or an alkoxycarbonyl group.

[claim12]
12. The bipyridyl compound according to claim 1, wherein when R2 is an unsubstituted C1-16 hydrocarbon group or a C1-16 hydrocarbon group substituted with a C1-10 alkyl group, a C3-7 cycoalkyl group or a phenyl group.
  • Inventor, and Inventor/Applicant
  • Kuninobu Yoichiro
  • Kanai Motomu
  • Ida Haruka
  • Nishi Mitsumi
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) ERATO KANAI Life Science Catalysis AREA
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