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Publication Type : Journal Article
Publisher : Advanced Synthesis & Catalysis, Volume 361, Issue 24, p.5661-5676 (2019)
Source : Advanced Synthesis & Catalysis, Volume 361, Issue 24, p.5661-5676 (2019)
Keywords : 5-Endo-trig radical cyclization, captodative-stabilization, Cu(I)-catalyst, NH-enamine, NH-Pyrrole
Campus : Amritapuri
School : School of Arts and Sciences
Department : Chemistry
Verified : Yes
Year : 2019
Abstract : 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.
Cite this Research Publication : R. N. Ram, Sandhya Sadanandan, and Gupta, D. Kumar, “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”, Advanced Synthesis & Catalysis, vol. 361, no. 24, pp. 5661-5676, 2019.