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. 2022 Jun 15;13(26):7947-7954.
doi: 10.1039/d2sc02291e. eCollection 2022 Jul 6.

Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light

Wan-Lei Yu  1   2 , Zi-Gang Ren  1 , Ke-Xing Ma  1 , Hui-Qing Yang  3 , Jun-Jie Yang  1 , Haixue Zheng  4 , Wangsuo Wu  2 , Peng-Fei Xu  1   4   2
Affiliations

Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light

Wan-Lei Yu et al. Chem Sci. .

Abstract

The transformations that allow the direct removal of hydrogen from their corresponding saturated counterparts by the dehydrogenative strategy are a dream reaction that has remained largely underexplored. In this report, a straightforward and robust cobaloxime-catalyzed photochemical dehydrogenation strategy via intramolecular HAT is described for the first time. The reaction proceeds through an intramolecular radical translocation followed by the cobalt assisted dehydrogenation without needing any other external photosensitizers, noble-metals or oxidants. With this approach, a series of valuable unsaturated compounds such as α,β-unsaturated amides, enamides and allylic and homoallylic sulfonamides were obtained in moderate to excellent yields with good chemo- and regioselectivities, and the synthetic versatility was demonstrated by a range of transformations. And mechanistic studies of the method are discussed.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Dehydrogenation strategies for alkene synthesis.
Scheme 2
Scheme 2. Proposed reaction mechanism.
See this image and copyright information in PMC

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