19731-70-5

Upstream product

• 1192-28-5 Cyclopentanone oxime 
• 100-44-7 benzyl chloride 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 120-92-3 cyclopentanone 
• 192139-56-3 1,1,3,3-tetraoxo-1λ⁶,3λ⁶-[1,3]dithiolan-2-one O-benzyl-oxime 
• 192139-55-2 [1,3]dithiolan-2-one O-benzyl-oxime 
• 192139-57-4 C₁₀H₁₃NOS₂ 
• 100-39-0 benzyl bromide 
• 628-21-7 1,4-Diiodobutane 
• 192139-47-2 bis(methylsulfonyl)methanone benzyloxime 

Downstream Products

• 937716-74-0 N-(1-cyclopentenyl)-2,2,2-trifluoro-N-(phenylmethoxy)acetamide 
• 1069074-20-9 diethyl {1-[(benzyloxy)amino]cyclopentyl}phosphonate 

Relevant academic research and scientific papers

Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical?radical cross-coupling powered by visible light photocatalysis

Transition-metal-catalyzed C?N bond-forming reactions have emerged as fundamental and powerful tools to construct arylamines, a common structure found in drug agents, natural products, and fine chemicals. Reported herein is an alternative access to heteroarylamine via radical?radical cross-coupling pathway, powered by visible light catalysis without any aid of external oxidant and reductant. Only by visible light irradiation of a photocatalyst, such as a metal-free photocatalyst, does the cascade single-electron transfer event for amines and heteroaryl nitriles occur, demonstrated by steady-state and transient spectroscopic studies, resulting in an amine radical cation and aryl radical anion in situ for C?N bond formation. The metal-free and redox economic nature, high efficiency, and site-selectivity of C?N cross-coupling of a range of available amines, hydroxylamines, and hydrazines with heteroaryl nitriles make this protocol promising in both academic and industrial settings.

Metal-Free 2,2,6,6-tetramethylpiperidin-1-yloxy radical (TEMPO) catalyzed aerobic oxidation of hydroxylamines and alkoxyamines to oximes and oxime ethers

TEMPO-Mediated oxidation of hydroxylamines (=hydroxyamines) and alkoxyamines to the corresponding oxime derivatives is reported (TEMPO=2,2,6,6-tetramethylpiperidin-1-yloxy radical; Scheme 2). These environmentally benign oxidations proceed in good to excellent yields (Table 1). For alkoxyamines, oxidation to the corresponding oxime ethers can be performed by using dioxygen as a terminal oxidant in the presence of 5-10 mol-% of TEMPO or 4-substituted derivatives thereof as a catalyst (Scheme 3 and Table 2). Importantly, benzyl bromides can directly be transformed to oxime ethers via in situ alkoxyamine formation by a nucleophilic substitution followed by TEMPO-mediated oxidation (Scheme 4 and Table 3). Copyright