Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO<sub>2</sub>-Reference-Cited by-同舟云学术

Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO₂

Published:2024-08-13 Issue:49 Volume:30 Page:
ISSN:0947-6539
Container-title:Chemistry – A European Journal
language:en
Short-container-title:Chemistry A European J

Author:

Brunetti Andrea¹²,Garbini Mauro¹²,Autuori Giuseppe¹,Zanardi Chiara³⁴,Bertuzzi Giulio¹²,Bandini Marco¹²

Affiliation:

1. Dipartimento di Chimica “Giacomo Ciamician” Alma Mater Studiorum Università di Bologna via P. Gobetti, 85 40129 Bologna Italy

2. Center for Chemical Catalysis, C³ Alma Mater Studiorum Università di Bologna via P. Gobetti, 85 40129 Bologna Italy

3. Department of Molecular Sciences and Nanosystems Ca' Foscari University of Venice via Torino, 155 30170 Venezia (Mestre) Italy

4. Institute for Organic Synthesis and Photoreactivity (ISOF) National Research Council of Italy (CNR) via P. Gobetti 101 40129 Bologna Italy

Abstract

AbstractLeveraging electrochemistry, a new synthesis of non‐natural derivatives of itaconic acid is proposed by utilizing carbon dioxide (CO2) as a valuable C1 synthon. An electrochemical cross‐electrophile coupling between allenoates and CO2 was targeted, allowing for the synthesis of both mono‐ and di‐carboxylation products in a catalyst‐ and additive‐free environment (yields up to 87 %, 30 examples). Elaboration of the model mono‐carboxylation product, and detailed cyclovoltammetric, as well as mechanistic analyses complete the present investigation.

Publisher

Wiley

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