Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light

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.

Graphical abstract: Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Apr 2022
Accepted
13 Jun 2022
First published
15 Jun 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022, Advance Article

Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light

W. Yu, Z. Ren, K. Ma, H. Yang, J. Yang, H. Zheng, W. Wu and P. Xu, Chem. Sci., 2022, Advance Article , DOI: 10.1039/D2SC02291E

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