American Chemical Society
jo9b01506_si_001.pdf (9.31 MB)

Stereospecific Copper(II)-Catalyzed Tandem Ring Opening/Oxidative Alkylation of Donor–Acceptor Cyclopropanes with Hydrazones: Synthesis of Tetrahydropyridazines

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journal contribution
posted on 2019-08-14, 17:08 authored by Manmath Mishra, Pinaki Bhusan De, Sourav Pradhan, Tharmalingam Punniyamurthy
Aerobic copper­(II)-catalyzed tandem ring opening and oxidative C–H alkylation of donor–acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper­(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89–98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper­(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.