1570134-84-7

Upstream product

• 433-97-6 2-trifluoromethylbenzoic acid 
• 1570134-65-4 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-3-methoxybenzamide 
• 1885-29-6 anthranilic acid nitrile 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 312-94-7 2-trifluoromethylbenzoyl chloride 

Downstream Products

• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 1570135-16-8 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-(4-methylphenylsulfonamido)-6-(trifluoromethyl)benzamide 

Relevant academic research and scientific papers

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.

Amide-Oxazoline Directed ortho-C–H Nitration Mediated by CuII

A CuII-mediated ortho-C–H nitration using amide-oxazoline as the directing group has been developed. The reactions utilize sodium nitrite as the source of the nitro group under O2 atmosphere and proceed smoothly. The desired products can be obtained in yields of 26–94 %.

Copper-Mediated Amination of Aryl C-H Bonds with the Direct Use of Aqueous Ammonia via a Disproportionation Pathway

The direct amination of C-H bonds with ammonia is a challenge in synthetic chemistry. Herein, we present a copper-mediated approach that enables a chelation-assisted aromatic C-H bond amination using aqueous ammonia. A key strategy was to use soft low-valent Cu(I) species to avoid the strong coordination of ammonia. Mechanistic investigations suggest that the catalysis is initiated by a facile deprotonation of bound ammonia, and the C-N coupling is achieved by subsequent reductive elimination of the resultant copper-amido intermediate from a Cu(III) intermediate that is readily generated by disproportionation of low-valent copper analogues. This mechanistic postulate was supported by a preliminary kinetic isotope effect study and computations. This new chelation-assisted, copper-mediated C-H bond amination with aqueous ammonia was successfully applied to a broad range of substrates to deliver primary anilines. Moreover, the mild conditions required for this transformation allowed the reaction to operate even under substoichiometric conditions to enable a late-stage application for the preparation of pharmaceutical agents.

Cu(II)-mediated ortho C-H alkynylation of (hetero)arenes with terminal alkynes

Cu(II)-promoted ortho alkynylation of arenes and heteroarenes with terminal alkynes has been developed to prepare aryl alkynes. A variety of arenes and terminal alkynes bearing different substituents are compatible with this reaction, thus providing an alternative disconnection to Sonogashira coupling.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.