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

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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.

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

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Article information


Submitted
04 Dec 2019
Accepted
11 Jan 2020
First published
13 Jan 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

M. Zhang, S. Li, J. Tu, Q. Min and F. Liu, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01446B

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