An on-surface Diels–Alder reaction
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ISSN: 1433-7851
E-ISSN: 1521-3773
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Wiley
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Abstract
The Diels–Alder reaction is one of the most popular reactions in organic chemistry. However, its use in the field of on-surface synthesis is hampered by the spatial restrictions of this cycloaddition reaction. Herein we selected a cyclic strained triyne to demonstrate an on-surface hexadehydro-Diels–Alder reaction in a single molecule. The reaction was studied in detail by means of atomic force microscopy (AFM) with CO-functionalized tips. Our results pave the way to use this iconic pericyclic reaction for on-surface synthesis, introducing the concept of atom economy in the field
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Angew. Chem. Int. Ed. 2021, 60, 26346 – 26350. https://doi.org/10.1002/anie.202110311
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https://doi.org/10.1002/anie.202110311Sponsors
We thank Rolf Allenspach and Enrique Guitián for discussions. We thank the European Union (Project SPRING, contract no. 863098), the ERC grant AMSEL (682144), the Spanish Agencia Estatal de Investigación (PID2019-107338RB-C62, PID2019-110037GB-I00 and PCI2019-111933-2), Xunta de Galicia (Centro de Investigación de Galicia accreditation 2019–2022, ED431G 2019/03) and the European Regional Development Fund-ERDF for financial support
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©2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is noncommercial and no modifications or adaptations are made