4.6 Article

Direct Aroylation of Olefins through a Cobalt/Photoredox-Catalyzed Decarboxylative and Dehydrogenative Coupling with α-Oxo Acids

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 72, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202202781

关键词

cobaloxime; decarboxylative; Hammett; hydrogen evolution; metallaphotoredox

资金

  1. National Science Foundation [CHE-1800147, CHE-2155003]
  2. Kansas Bioscience Authority Rising Star program
  3. NSF Academic Research Infrastructure Grant [9512331]
  4. NIH Shared Instrumentation Grant [S10RR024664]
  5. NSF Major Research Instrumentation Grant [0320648]
  6. Direct For Biological Sciences
  7. Div Of Biological Infrastructure [9512331] Funding Source: National Science Foundation

向作者/读者索取更多资源

A dual catalytic procedure involving photoredox and cobalt catalysts has been developed for the benzoylation of olefins. The photoredox catalyst initiates the decarboxylation of alpha-ketoacids to generate benzoyl radicals, which react with styrenes in the presence of a cobalt catalyst that abstracts a hydrogen atom. The catalytic system allows a Heck-like aroylation without the need for a stoichiometric oxidant. Mechanistic studies show that differently substituted styrenes result in a curved Hammett plot, suggesting a change in the product-determining step in the catalytic mechanism.
A photoredox/cobalt dual catalytic procedure has been developed that allows benzoylation of olefins. Here the photoredox catalyst effects the decarboxylation of alpha-ketoacids to form benzoyl radicals. After addition of this radical to styrenes, the cobalt catalyst abstracts a H-atom. Hydrogen evolution from the putative cobalt hydride intermediate allows a Heck-like aroylation without the need for a stoichiometric oxidant. Mechanistic studies reveal that electronically different styrenes lead to a curved Hammett plot, thus suggesting a change in product-determining step in the catalytic mechanism.

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