4.8 Article

Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light

期刊

CHEMICAL SCIENCE
卷 13, 期 26, 页码 7947-7954

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2sc02291e

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资金

  1. NSFC [21632003, 21871116, 22071085]
  2. Key Program of Gansu Province [17ZD2GC011]
  3. 111 Program from the MOE of P. R. China

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This study describes a cobaloxime-catalyzed photochemical dehydrogenation strategy for the direct removal of hydrogen atoms from saturated compounds. The reaction shows good yields, selectivity, and synthetic versatility without the need for external photosensitizers, noble metals, or oxidants, making it potentially useful for synthesis.
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 alpha,beta-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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