70123-10-3

Upstream product

• 60721-36-0 N-{(2,2,2-trichloro-1-phenylethyl)}acetamide 

Downstream Products

• 136454-72-3 triphenyl(1-phenyl-2,2,2-trichloroethylideneamino)phosphonium chloride 
• 136454-70-1 1-(Benzenesulfonylamido)-1-phenyl-2,2,2-trichloroethane 
• 136454-71-2 N,N-dichloro-1-phenyl-2,2,2-trichloroethylamine 

Relevant academic research and scientific papers

β,β,β-Trichloroethyl-NH-Enamine as Viable System for 5-Endo-trig Radical Cyclization via Multifaceted CuI?CuII Redox Catalysis: Single Step Synthesis of Multi-Functionalized NH-Pyrroles

Here we report a mild and regioselective copper-catalyzed direct synthesis of multi-substituted and functionalized NH-pyrroles in high yields from diverse β,β,β-trichloroethyl-NH-enamines via a novel 5-endo-trig radical cyclization mode, previously known to be unviable in the enamine system. An approach to transform a geometrically ‘disfavored to favored’ 5-endo-trig radical cyclization mode in NH-enamine systems via multifaceted CuI?CuII redox catalysis generating radicals, preventing dehalogenative reduction of radical precursors and dehydrohalogenating the 5-endo-trig cyclized products have been demonstrated experimentally. With wider substrate scope, this method incorporates halo-, NH- and carbonyl functionalities besides alkyl, aryl and heteroaryl substituents in the pyrrole unit easily. These difficult to prepare 3-halo-NH-pyrroles are potential sources for natural products, agrochemicals, pharmaceuticals and organometallic chemistry.