17064-22-1

Upstream product

• 532-28-5 (RS)-mandelonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 696-62-8 para-iodoanisole 
• 1006-68-4 5-phenyloxazole 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 156780-52-8 2-(4-methoxyphenyl)-1,3-oxazole 
• 591-50-4 iodobenzene 
• 3532-17-0 4-methoxybenzoyl azide 
• 536-74-3 phenylacetylene 
• 6346-07-2 4-methoxy-N-(2-phenylethyl)benzamide 
• 100-09-4 4-methoxybenzoic acid 
• 623-12-1 4-chloromethoxybenzene 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 100-42-5 styrene 

Downstream Products

• 3672-52-4 3-(4-methoxyphenyl)-5-phenylisoxazole 
• 62921-40-8 4-(4-methoxy-phenyl)-5-phenyl-oxazole 
• 84591-13-9 2-(p-hydroxyphenyl)-5-phenyloxazole 

Relevant academic research and scientific papers

Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling

Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.

Synthesis method of oxazole heterocyclic compound

The invention belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of an oxazole heterocyclic compound. Aryl aldehyde and a triazole derivative are used as raw materials and are heated to react in the presence of trichloromethane and rhodium acetate catalysts to obtain the oxazole heterocyclic compound. By using the method provided by the invention, under the condition of heating and stirring, the oxazole heterocyclic derivative can be obtained at a relatively high yield after reaction for 3-12 hours. According to the method disclosed by the invention, the oxazole heterocyclic derivative is simply, conveniently and efficiently synthesized by using simple and easily available raw materials through a one-step method, and a simple and efficient new synthesis method with wide substrate universality is provided for synthesizing the oxazole heterocyclic derivative.

Ni-Catalyzed C-H Arylation of Oxazoles and Benzoxazoles Using Pharmaceutically Relevant Aryl Chlorides and Bromides

This manuscript details the development of the nickel-catalyzed arylation of oxazoles and benzoxazoles with aryl halides. A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications were surveyed. The desired arylated products were obtained in synthetically useful yields using electronically and structurally varied aryl halides. The use of microscale high-throughput experimentation was essential for both the rapid identification of optimal reaction parameters and the investigation of the aryl halide scope.

Divergent Conversion of N-Acyl-isoxazol-5(2 H)-ones to Oxazoles and 1,3-Oxazin-6-ones Using Photoredox Catalysis

The fragmentation of N-acyl-isoxazol-5-ones using visible light photoredox catalysis has been disclosed. The catalyst-controlled divergent mechanisms, namely the oxidative and reductive quenching catalytic cycle, are utilized. Various oxazoles and 1,3-oxazin-6-ones are selectively obtained from the same isoxazol-5-one skeleton under mild conditions.

CO2/Photoredox-Cocatalyzed Tandem Oxidative Cyclization of α-Bromo Ketones and Amines to Construct Substituted Oxazoles

CO2/photoredox-cocatalyzed tandem oxidative cyclization of α-bromo ketones and amines for the preparation of substituted oxazoles has been achieved. The avoidance of using both transition-metal catalysts and peroxides makes this method more sustainable and renewable.

Metal-free iodine(iii)-promoted synthesis of 2,5-diaryloxazoles

A nonmetal-catalyzed oxidative cyclization to achieve 2,5-disubstituted oxazoles from inexpensive and readily available substituted chalcone, (diacetoxyiodo)benzene (PIDA) and ammonium acetate (NH4OAc) at room temperature is described. The reaction forms a variety of 2,5-diaryloxazoles in good to excellent yields with broad substrate scope under mild conditions without the requirement of ligands and additional bases.

Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis

A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available α-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)3]Cl2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also demonstrated by preparing a natural product, texaline.

A facile synthesis of 2,5-disubstituted oxazoles via a copper-catalyzed cascade reaction of alkenes with azides

A novel and efficient approach to the synthesis of 2,5-disubstituted oxazoles is developed via a 1,3-dipolar cycloaddition/ring cleavage/1,2-H migration/denitrogenation/copper-catalyzed aerobic oxidative dehydrogenative cyclization cascade. The desired products can be obtained from readily available aromatic terminal alkenes and azides employing air as the oxidant under mild conditions, and it offers an attractive alternative method for the synthesis of oxazole derivatives.

Iodine catalysed intramolecular C(sp3)-H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides

Iodine catalyzed synthesis of 2,5-disubstituted oxazoles from N-arylethylamides through intramolecular C(sp3)-H functionalization under metal-free conditions is described. The method is tolerable to a wide range of substrates having a variety of functional groups with moderate to good yields of the products.

Reaction of alkynes and azides: Not triazoles through copper-acetylides but oxazoles through copper-nitrene intermediates

Well-defined copper(I) complexes of composition [Tpm* ,BrCu(NCMe)]BF4 (Tpm*,Br=tris(3,5- dimethyl-4-bromo-pyrazolyl)methane) or [Tpa* Cu]PF6 (Tpa=tris(3,5-dimethyl-pyrazolylmethyl)amine) catalyze the formation of 2,5-disubstituted oxazoles from carbonyl azides and terminal alkynes in a direct manner. This process represents a novel procedure for the synthesis of this valuable heterocycle from readily available starting materials, leading exclusively to the 2,5-isomer, attesting to a completely regioselective transformation. Experimental evidence and computational studies have allowed the proposal of a reaction mechanism based on the initial formation of a copper-acyl nitrene species, in contrast to the well-known mechanism for the copper-catalyzed alkyne and azide cycloaddition reactions (CuAAC) that is triggered by the formation of a copper-acetylide complex.