Photo-hydroacylation: 1-tetralones from ortho-allylbenzaldehydes

文献信息

发布日期 2023-10-10
DOI 10.1039/D3QO01510F
影响因子 5.281
作者

Veronika Schmalz, Ulrich Koert


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摘要

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.

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DOI: 10.1039/C4CP90007C

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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