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 des 2022
Accepted
02 jan 2023
First published
26 jan 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements