Issue 23, 2023
From the journal:

Organic Chemistry Frontiers

Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes†

Veronika Schmalza  and  Ulrich Koert ORCID logo *a  

* Corresponding authors

a Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein Straße 4, 35043 Marburg, Germany
E-mail: koert@chemie.uni-marburg.de

Abstract

A light-induced intramolecular hydroacylation of ortho-allylbenzaldehydes is presented, yielding the selective formation of a six-membered ring in 1-tetralones. The photo-hydroacylation proceeds at 365 nm, ambient temperature, and additive-free conditions. The proposed mechanistic pathway involves a light-induced 1,5-hydrogen atom transfer (1,5-HAT) and a radical recombination process leading to the formation of the 1-tetralone product. Deuteration and radical-clock experiments support the mechanism. This efficient photo-hydroacylation provides a valuable method for the synthesis of various tetralone scaffolds through light activation.

Graphical abstract: Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes

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Article information

DOI
https://doi.org/10.1039/D3QO01510F
Article type
Research Article
Submitted
15 Sep 2023
Accepted
10 Oct 2023
First published
10 Oct 2023

Org. Chem. Front., 2023,10, 5870-5875

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Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes

V. Schmalz and U. Koert, Org. Chem. Front., 2023, 10, 5870 DOI: 10.1039/D3QO01510F

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