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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.

SUBMITTER: Yamamoto H

PROVIDER: S-EPMC10583705 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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

Yamamoto Hiroki H Yamaoka Kohei K Shinohara Ann A Shibata Kouhei K Takao Ken-Ichi KI Ogura Akihiro A

Chemical science 20230928 40

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 <i>via</i> Dexter energy transfer ...[more]

PMID: 37860659

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Dataset Information

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

Publications

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

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