Merging the Norrish type I reaction and transition metal catalysis: photo- and Rh-promoted borylation of C-C σ-bonds of aryl ketones

Chem Sci. 2023 Jan 26;14(8):1960-1965. doi: 10.1039/d2sc06801j. eCollection 2023 Feb 22.

ABSTRACT

Synthesis of arylboronates via borylation of C-C σ-bonds of aryl ketones was achieved by the combined use of photoenergy and a Rh catalyst. The cooperative system enables α-cleavage of photoexcited ketones to generate aroyl radicals via the Norrish type I reaction, which are successively decarbonylated and borylated with the rhodium catalyst. This work establishes a new catalytic cycle merging the Norrish type I reaction and Rh catalysis and demonstrates the new synthetic utility of aryl ketones as aryl sources for intermolecular arylation reactions.

PMID:36845921 | PMC:PMC9945184 | DOI:10.1039/d2sc06801j

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