Issue 8, 2023

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

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Dec. 2022
Accepted
02 Janv. 2023
First published
26 Janv. 2023
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., 2023,14, 1960-1965

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

Y. Fujimaki, N. Iwasawa and J. Takaya, Chem. Sci., 2023, 14, 1960 DOI: 10.1039/D2SC06801J

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