778581-67-2

Upstream product

• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 92629-11-3 5-bromo-2-phenyl-1,3-oxazole 
• 1194627-95-6 2-nitro-1-(4-(trifluoromethyl)phenyl)ethan-1-one 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 2996-92-1 phenyl trimethylsiloxane 
• 87150-14-9 5-(4-(trifluoromethyl)phenyl)oxazole 
• 874813-04-4 2-azido-1-[4-(trifluoromethyl)phenyl]-1-ethanone 
• 1299491-27-2 2-(N-benzoylamino)-1-[4-(trifluoromethyl)phenyl]-1-ethanone 
• 383-53-9 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone 
• 100-46-9 benzylamine 
• 59722-32-6 (3-hydroxyphenyl)methanesulfonate 
• 4920-92-7 pivalic acid phenyl ester 
• 16156-59-5 phenyl methanesulfonate 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 

Downstream Products

• 1299491-15-8 (R)-N-[2-hydroxy-2-{4-(trifluoromethyl)phenyl}ethyl]benzamide 
• 1299491-31-8 C₂₅H₂₂F₃NO₄ 
• 1299491-35-2 C₂₅H₂₂F₃NO₄ 
• 1299491-08-9 (R)-2-phenyl-5-[4-(trifluoromethyl)phenyl]oxazoline 
• 1260140-57-5 2-(1,2,3,4,5,6,7,8-octaphenylanthracen-9-yl)-5-(4-trifluoromethylphenyl)oxazole 

Relevant academic research and scientific papers

Nickel-catalyzed C?H arylation of benzoxazoles and oxazoles: Benchmarking the influence of electronic, steric and leaving group variations in phenolic electrophiles

Electronic, steric and leaving group effects for Ni-catalyzed direct arylations using C?O electrophiles were benchmarked. The scope of arylations with pivalates was general with respect to both the electronics on the electrophile and the azoles. Furthermore, the arylation of azoles with tosylates, mesylates and carbamates with varying electronics was explored, and showed electronic trends similar to those of the pivalate reactions. Finally, the relative rate of arylation of 5-methyl benzoxazole with two electronically-similar electrophiles bearing different leaving groups was established. The results from these studies implicate the following order of relative reactivity: mesylates>pivalates>carbamates.

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.

Metal-Free sp3 C-H Functionalization: PABS/I2-Promoted Synthesis of Polysubstituted Oxazole Derivatives from Arylethanones and 2-Amino-2-alkyl/arylacetic Acid

A nonmetal-catalyzed process for the synthesis of polysubstituted oxazoles from inexpensive and readily available α-amino acids and methyl ketones is established. This reaction is proposed to achieve oxidative cleavage of C(sp3)-H bonds, followed by decarboxylation and annulation. The mild reaction conditions employed in both cases enable the tolerance of a wide range of functional groups as well as high reaction efficiency.

Copper-catalyzed oxidative cyclization of chalcone and benzylic amine leading to 2,5-diaryl oxazoles via carbon-carbon double bond cleavage

A copper-catalyzed oxidative cyclization of chalcone with benzylic amine is achieved, providing 2,5-diaryl oxazoles in moderate to good yields. The procedure employs O2 as a clean oxidant and involves an oxidative cleavage of the CC bond as the key step.

Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles

Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated

Nickel-catalyzed direct C-H arylation and alkenylation of heteroarenes with organosilicon reagents

"Chemical Equation Presented" Breaking the Si-lence: The direct crosscoupling of heteroarenes with aryl- or alkenylsilanes proceeds efficiently, in the presence of a nickel catalyst, to create a wide range of aryl- and alkenyl-heteroaryl bonds efficiently (see scheme; DMAc= N.N-dimethylacetamide, bpy = 2,2′-bipyridine). This catalysis represents a new avenue for using organosilanes in the catalytic C-H functionalization chemistry.

C-H bond activation: A versatile protocol for the direct arylation and alkenylation of oxazoles

The versatile palladium, complex Pd(PPh3)4 catalyses both direct arylation and alkenylation of oxazoles efficiently. The method is regioselective and stereospecific with respect to bromoalkenes and tolerates a wide range of functional groups.

Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones

One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)3 (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)3 in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields.

General facile synthesis of 2,5-diarylheteropentalenes

Palladium-catalyzed cross-coupling reactions of various heteropentalene derivatives were systematically studied. A general three-step synthesis of 2,5-diarylheteropentalenes involving two Suzuki or Negishi couplings and a regiospecific bromination was developed. Nonsymmetrical 2,5-diaryl-furans, thiophenes, pyrroles, 1,3-thiazoles, 1,3-oxazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles were prepared in 31-67% isolated yield (three steps).