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Metal-free iminyl radical-mediated C–C single bond cleavage/functionalization of redox-active oxime esters

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A visible-light-driven iminyl radical-mediated C–C bond cleavage and functionalization of cycloketone oxime esters have been accomplished. This protocol is simple and does not require expensive and toxic photoredox and/or transition-metal… Click to show full abstract

A visible-light-driven iminyl radical-mediated C–C bond cleavage and functionalization of cycloketone oxime esters have been accomplished. This protocol is simple and does not require expensive and toxic photoredox and/or transition-metal catalysis, providing a novel catalyst-free strategy for alkylation, allylation, vinylation and alkynylation through addition of C(sp3)-centered radicals to various unsaturated acceptors. The commercially available and photoactive Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Keywords: iminyl radical; oxime esters; bond cleavage; radical mediated; cleavage functionalization

Journal Title: Organic chemistry frontiers
Year Published: 2020

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