Issue 40, 2023

Red-light-mediated Barton decarboxylation reaction and one-pot wavelength-selective transformations

Abstract

In organic chemistry, selecting mild conditions for transformations and saving energy are increasingly important for achieving sustainable development goals. Herein, we describe a red-light-mediated Barton decarboxylation using readily available red-light-emitting diodes as the energy source and zinc tetraphenylporphyrin as the catalyst, avoiding explosive or hazardous reagents or external heating. Mechanistic studies suggest that the reaction probably proceeds via Dexter energy transfer between the activated catalyst and the Barton ester. Furthermore, a one-pot wavelength-selective reaction within the visible light range is developed in combination with a blue-light-mediated photoredox reaction, demonstrating the compatibility of two photochemical transformations based on mechanistic differences. This one-pot process expands the limits of the decarboxylative Giese reaction beyond polarity matching.

Graphical abstract: Red-light-mediated Barton decarboxylation reaction and one-pot wavelength-selective transformations

Supplementary files

Article information

Article type
Edge Article
Submitted
15 Jul 2023
Accepted
18 Sep 2023
First published
28 Sep 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 license

Chem. Sci., 2023,14, 11243-11250

Red-light-mediated Barton decarboxylation reaction and one-pot wavelength-selective transformations

H. Yamamoto, K. Yamaoka, A. Shinohara, K. Shibata, K. Takao and A. Ogura, Chem. Sci., 2023, 14, 11243 DOI: 10.1039/D3SC03643J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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