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US 2026/0308125 A1Published application
Heterocyclic carboxylic acid hydrazide ligand and use thereof in copper-catalyzed aryl halide coupling reaction
AssigneeShanghai Institute of Organic Chemistry, Chinese Academy of Sciences
InventorsDawei MA, Lanting XU, Sailuo LI, Hua SHAO, Xiang LI
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Abstract
A heterocyclic carboxylic acid hydrazide ligand and the use thereof in copper-catalyzed aryl halide coupling reaction are provided. Specifically, the compound of formula 1 can be used as a ligand in the copper-catalyzed aryl halide coupling reaction, and is used for catalyzing a coupling reaction for forming aryl halides such as C—N, C—O, C—S and C—C bonds.
Claims11
The method of a compound as shown in formula I, and isomers thereof:
- wherein, A is a saturated or unsaturated C5-C6 carbocyclyl, or a saturated or unsaturated 5 - or 6-membered carbon heterocarbocyclyl, or a benzo saturated or unsaturated 5- or 6-membered carbon heterocarbocyclyl, wherein the carbon heterocarbocyclyl has 1 to 5 heteroatoms selected from the group consisting of:
- N, O, and S;
- A is optionally substituted by substituents selected from the group consisting of:
- hydroxyl, nitro,—NRaRb, halogen, C1-4 alkyl, C1-4 alkoxy, phenyl, and oxo (i.e., two hydrogen atoms on the same carbon atom in the group are replaced by ═O);
- Ra and Rb are each independently selected from the group consisting of:
- H, hydroxyl, amino, halogen, and C1-4 alkyl;
- R1 and R2 are each independently selected from the group consisting of:
- H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted 3- to 6-membered heterocyclyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5- to 20-membered heteroaryl, and substituted or unsubstituted benzyl;
- or, R1 and R2, together with the N atom to which they are attached, form a 3- to 20-membered saturated or unsaturated carbocycle or heterocycle (such as substituted or unsubstituted pyrrole, indole, azoles, benzazole, and aromatic heterocycle);
- characterized in that it is used as a ligand in copper-catalyzed coupling reactions of aryl halide;
- wherein, the aryl halide is selected from the group consisting of:
- aryl chloride, aryl bromide, aryl iodide, or a combination thereof;
- unless otherwise specified, the “substituted” refers to one or more hydrogen atoms in the group being substituted with substituents selected from the group consisting of:
- C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, 3- to 20-membered heteroaryl, C6-C10 aryl-O—, halogen, nitro, hydroxyl, cyano, C2-C10 ester group (alkyl-COO—), C2-C10 acyl (alkyl-CO—), sulfonate, or two hydrogen atoms on two adjacent carbon atoms in the group are replaced by —(CH2)n— (n is 1, 2, 3, 4, 5 or 6).
11 more elements
A compound as shown in formula I;
- wherein, A is a saturated or unsaturated C5-C6 carbocycle, or a 5- or 6-membered carbon heterocarbocycle, or a benzo saturated or unsaturated 5- or 6-membered carbon heterocarbocycle, wherein the carbon heterocarbocycle has 1 to 5 heteroatoms selected from the group consisting of:
- N, O, and S;
- A is optionally substituted by substituents selected from the group consisting of:
- hydroxyl, nitro, —NRaRb, halogen, C1-4 alkyl, C1-4 alkoxy, phenyl, and oxo (i.e., two hydrogen atoms on the same carbon atom in the group are replaced by ═O);
- Ra and Rb are each independently selected from the group consisting of:
- H, hydroxyl, amino, halogen, and C1-4 alkyl;
- R1 and R2 are each independently selected from the group consisting of:
- H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C6 alkoxy, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted 3- to 6-membered heterocyclyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 5- to 20-membered heteroaryl, substituted or unsubstituted benzyl;
- or, R1 and R2, together with the N atom to which they are attached, form a 3- to 20-membered saturated or unsaturated carbocycle or heterocycle;
- unless otherwise specified, the “substituted” refers to one or more hydrogen atoms in the group being substituted with substituents selected from the group consisting of:
- C1-C6 alkyl, C1-C6 alkoxy, C6-C10 aryl, 3- to 20-membered heteroaryl, C6-C10 aryl-O—, halogen, nitro, hydroxyl, cyano, C2-C10 ester group (alkyl-COO—), C2-C10 acyl (alkyl-CO—), sulfonate, or two hydrogen atoms on two adjacent carbon atoms in the group are replaced by —(CH2)n— (n is 1, 2, 3, 4, 5 or 6).
8 more elements
Dependencies are inferred from the claim text.