Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones

[Image: see text] While electrocatalyzed alkyne annulations of arenes represent a powerful strategy for the assembly of heteroaromatic motives, electrochemical C(sp(2))–H activations of alkenes remain scarce. Herein, a strategy for the rhodaelectro-catalyzed functionalization of enamides is presente...

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Autores principales: Homölle, Simon L., Stangier, Maximilian, Reyes, Efraim, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: University of Science and Technology of China and American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10466456/
https://www.ncbi.nlm.nih.gov/pubmed/37654809
http://dx.doi.org/10.1021/prechem.3c00061
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author Homölle, Simon L.
Stangier, Maximilian
Reyes, Efraim
Ackermann, Lutz
author_facet Homölle, Simon L.
Stangier, Maximilian
Reyes, Efraim
Ackermann, Lutz
author_sort Homölle, Simon L.
collection PubMed
description [Image: see text] While electrocatalyzed alkyne annulations of arenes represent a powerful strategy for the assembly of heteroaromatic motives, electrochemical C(sp(2))–H activations of alkenes remain scarce. Herein, a strategy for the rhodaelectro-catalyzed functionalization of enamides is presented for the efficient construction of pyrroles using electricity as a sustainable oxidant. Moreover, the tuning of the solvent system allowed a fascinating switch in chemoselectivity, which is not possible with traditionally used chemical oxidants, giving rise to lactone architectures. The rhoda-electrocatalysis features a broad scope as well as high regio- and chemoselectivities.
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spelling pubmed-104664562023-08-31 Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones Homölle, Simon L. Stangier, Maximilian Reyes, Efraim Ackermann, Lutz Precis Chem [Image: see text] While electrocatalyzed alkyne annulations of arenes represent a powerful strategy for the assembly of heteroaromatic motives, electrochemical C(sp(2))–H activations of alkenes remain scarce. Herein, a strategy for the rhodaelectro-catalyzed functionalization of enamides is presented for the efficient construction of pyrroles using electricity as a sustainable oxidant. Moreover, the tuning of the solvent system allowed a fascinating switch in chemoselectivity, which is not possible with traditionally used chemical oxidants, giving rise to lactone architectures. The rhoda-electrocatalysis features a broad scope as well as high regio- and chemoselectivities. University of Science and Technology of China and American Chemical Society 2023-07-20 /pmc/articles/PMC10466456/ /pubmed/37654809 http://dx.doi.org/10.1021/prechem.3c00061 Text en © 2023 The Authors. Co-published by University of Science and Technology of China and American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Homölle, Simon L.
Stangier, Maximilian
Reyes, Efraim
Ackermann, Lutz
Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones
title Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones
title_full Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones
title_fullStr Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones
title_full_unstemmed Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones
title_short Bifurcated Rhodaelectro-catalyzed C–H Activation for the Synthesis of Pyrroles and Lactones
title_sort bifurcated rhodaelectro-catalyzed c–h activation for the synthesis of pyrroles and lactones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10466456/
https://www.ncbi.nlm.nih.gov/pubmed/37654809
http://dx.doi.org/10.1021/prechem.3c00061
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