96907-62-9

Upstream product

• 96907-77-6 1-(4-tolyl)-4-(4-methoxyphenyl)-2-aza-1,4-butanedione 
• 123-11-5 4-methoxy-benzaldehyde 
• 143949-80-8 N-(Benzotriazol-1-ylmethyl)-4-methylbenzamide 
• 619-55-6 para-methylbenzamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 22693-32-9 4-methylbenzoyl azide 
• 766-97-2 4-n-methylphenylacetylene 
• 1011-51-4 5-(4-methoxyphenyl)-1,3-oxazole 
• 624-31-7 4-tolyl iodide 
• 352-32-9 p-fluorotoluene 
• 16208-17-6 2,2-dihydroxy-1-(4-methoxyphenyl)ethan-1-one 
• 104-84-7 para-methylbenzylamine 

Relevant academic research and scientific papers

Ni-Catalyzed C?F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles

A Ni-catalyzed C?F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system.

Mechanistic Insights into Pincer-Ligated Palladium-Catalyzed Arylation of Azoles with Aryl Iodides: Evidence of a PdII-PdIV-PdII Pathway

Pincer-based (R2POCNR′2)PdCl complexes along with CuI cocatalyst catalyze the arylation of azoles with aryl iodides to give the 2-arylated azole products. Herein, we report an extensive mechanistic investigation for the direct arylation of azoles involving a well-defined and highly efficient (iPr2POCNEt2)PdCl (2a) catalyst, which emphasizes a rare PdII-PdIV-PdII redox catalytic pathway. Kinetic studies and deuterium labeling experiments indicate that the C-H bond cleavage on azoles occurs via two distinct routes in a reversible manner. Controlled reactivity of the catalyst 2a underlines the iodo derivative (iPr2POCNEt2)PdI (3a) to be the resting state of the catalyst. The intermediate species (iPr2POCNEt2)Pd-benzothiazolyl (4a) has been isolated and structurally characterized. A determination of reaction rates of compound 4a with electronically different aryl iodides has revealed the kinetic significance of the oxidative addition of the C(sp2)-X electrophile, aryl iodide, to complex 4a. Furthermore, the reactivity behavior of 4a suggests that the arylation of benzothiazole proceeds via an oxidative addition/reductive elimination pathway involving a (iPr2POCNEt2)PdIV(benzothiazolyl)(Ar)I species, which is strongly supported by DFT calculations.

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.

Metal-free dual sp3 C-H functionalization: I2- promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

An I2-promoted sp3 C-H functionalization has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available methyl ketones and benzylamines without any metal and peroxide catalyst. This domino oxidative cyclization process involves the cleavage of C-H bond and the formation of C-N, C-O bonds.

Palladium-catalyzed desulfitative arylation of azoles with arylsulfonyl hydrazides

Palladium-catalyzed desulfitative and denitrogenative arylation of azoles with arylsulfonyl hydrazides has been achieved. A broad scope of azoles and arylsulfonyl hydrazides has been used to produce arylated azoles in high yields.

Novel syntheses of polysubstituted pyrroles and oxazoles by 1,3-dipolar cycloaddition reactions of benzotriazole-stabilized nitrile ylides

1,3-Dipolar cycloadditions of benzotriazole-stabilized nitrile ylides with benzyl α,β-unsaturated-carboxylates and aldehydes as dipolarophiles proceeded smoothly and efficiently to give polysubstituted pyrroles and oxazoles, respectively, in good yields.

SYNTHESIS AND STUDY OF THE TRANSFER OF SUBSTITUENT ELECTRONIC EFFECTS IN SUBSTITUTED 2,5-DIPHENYLOXAZOLES

A series of para-substituted 2,5-diphenyloxazoles was synthesized using Robinson-Gabriel procedure and the transfer of substituent electronic effects in these compounds was examined.