81187-69-1

Upstream product

• 176503-80-3 1-benzoylamino-2-chloro-1-phenylethane 
• 100-52-7 benzaldehyde 
• 103738-73-4 N-<1-(methylthio)benzylidene>-1-(trimethylsilyl)methylamine 
• 75526-14-6 N-(2,2-dichloro-1-phenylethyl)benzamide 
• 6316-07-0 N-(2,2,2-trichloro-1-hydroxyethyl)benzamide 
• 98-88-4 benzoyl chloride 
• 1646327-66-3 C₂₁H₁₉NOSe 
• 591-50-4 iodobenzene 
• 119072-55-8 tert-butylisonitrile 
• 20989-17-7 Phenylglycinol 
• 100-47-0 benzonitrile 
• 60-12-8 2-phenylethanol 
• 65-85-0 benzoic acid 
• 100-42-5 styrene 

Downstream Products

• 96392-53-9 N-(2-hydroxy-1-phenylethyl)benzamide 
• 838-41-5 2,4-diphenyl-1,3-oxazole 

Relevant academic research and scientific papers

Photochemical Transformation of O-(β-Arylethyl) Arylimidates into 2,4-Diaryl-5-iodoxazoles with 1,3-Diiodo-5,5-dimethylhydantoin

Treatment of O-(β-arylethyl) arylimidates with 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation with a tungsten lamp in 1,2-dichloroethane gave the corresponding 2,4-diaryl-5-iodoxazoles and 2,4-diaryloxazoles in good to moderate yields, respectively, depending on the aryl group. It was proposed that the reactions proceeded through the formation of N-iodoimidates by the reaction of O-(β-arylethyl) arylimidates with DIH, followed by the formation of iminyl radicals via homolytic N–I bond cleavage, the 1,5-H shift by the iminyl radicals, the C–I bond formation of the formed carbon-centered radicals with iodine, the nucleophilic cyclization by the imino groups to form 2,4-diaryloxazolines, the oxidation of the formed 2,4-diaryloxazolines to 2,4-diaryloxazoles, and the iodination of the formed 2,4-diaryloxazoles to 2,4-diaryl-5-iodoxazoles with DIH.

Radical cascade synthesis of azoles: via tandem hydrogen atom transfer

A radical cascade strategy for the modular synthesis of five-membered heteroarenes (e.g. oxazoles, imidazoles) from feedstock reagents (e.g. alcohols, amines, nitriles) has been developed. This double C-H oxidation is enabled by in situ generated imidate

Site-Specific C(sp3)–H Aminations of Imidates and Amidines Enabled by Covalently Tethered Distonic Radical Anions

The utilization of N-centered radicals to synthesize nitrogen-containing compounds has attracted considerable attention recently, due to their powerful reactivities and the concomitant construction of C?N bonds. However, the generation and control of N-centered radicals remain particularly challenging. We report a tethering strategy using SOMO-HOMO-converted distonic radical anions for the site-specific aminations of imidates and amidines with aid of the non-covalent interaction. This reaction features a remarkably broad substrate scope and also enables the late-stage functionalization of bioactive molecules. Furthermore, the reaction mechanism is thoroughly investigated through kinetic studies, Raman spectroscopy, electron paramagnetic resonance spectroscopy, and density functional theory calculations, revealing that the aminations likely involve direct homolytic cleavage of N?H bonds and subsequently controllable 1,5 or 1,6 hydrogen atom transfer.

XtalFluor-E: An Efficient Reagent for Synthesis of Oxazolines from Carboxylic Acids and O-Silylated Amino Alcohols

An efficient protocol has been developed for the synthesis of 2-oxazolines from carboxylic acids and silylated amino alcohols. The advantage of this method was demonstrated by preparing O-silylated amino alcohols. The reaction proceeds via in situ desilylation of O-silylated amide followed by cyclization. Studies on silyl deprotection were carried out to explain yield for 2-oxazolines.

Radical-mediated intramolecular β-C(sp3)-H amidation of alkylimidates: Facile synthesis of 1,2-amino alcohols

A new radical-mediated intramolecular β-C(sp3)-H amidation reaction of O-alkyl trichloro- or arylimidates is reported. Various oxazolines were efficiently prepared from easily accessible alcohol starting materials. The trichloro-oxazoline products can be hydrolyzed under mild conditions to give valuable 1,2-amino alcohols. This amidation reaction exhibits a broad substrate scope and good functional group tolerance, and offers a powerful means for the C(sp3)-H functionalization of alcohols. Mechanistic studies suggest that a sequence of 1,5-HAT of an imidate radical, iodination and cyclization might be operative.

Directed β C-H Amination of Alcohols via Radical Relay Chaperones

A radical-mediated strategy for β C-H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C-H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Nickel-catalyzed ligand-free synthesis of benzoxazoles and oxazolines via isocyanide insertion

A novel and efficient route to benzoxazoles and oxazolines involving a nickel-catalyzed three-component coupling reaction of iodobenzene, an amino alcohol and tert-butyl isocyanide has been developed. A wide array of products have been prepared in good to excellent yields in the absence of ligand.

Magnesium bis(monoperoxyphthalate) hexahydrate as mild and efficient oxidant for the synthesis of selenones

A new, efficient and mild method for the direct oxidation of selenides to selenones using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) has been developed. Noteworthy this transformation proceeds at room temperature, employs a cheap and safety oxi

Stereoselective one-pot synthesis of oxazolines

(Chemical Equation Presented) Treatment of alkenes with NBS, a nitrile, NaHCO3 and water in the presence of Cu(OTf)2 or Zn(OTf)2 is reported to furnish oxazolines in one pot and good yields. The reaction is equally applica

A new synthetic route to 2-oxazolines. The electrochemical reduction of N-(2,2-dichloroethyl)amides as a key step

A convenient new method for the synthesis of 2-oxazolines has been established involving the preparation of N-(2,2-dichloroethyl)amides followed by electrochemical reductive cyclizations. It has been applied successfully in preparing previously unknown 4-