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An On-surface Diels-Alder Reaction

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Specialty Chemistry
Date 2021 Oct 19
PMID 34664770
Citations 3
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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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References
1.
Hoye T, Baire B, Niu D, Willoughby P, Woods B . The hexadehydro-Diels-Alder reaction. Nature. 2012; 490(7419):208-12. PMC: 3538845. DOI: 10.1038/nature11518. View

2.
Wackerlin C, Gallardo A, Mairena A, Baljozovic M, Cahlik A, Antalik A . On-Surface Hydrogenation of Buckybowls: From Curved Aromatic Molecules to Planar Non-Kekulé Aromatic Hydrocarbons. ACS Nano. 2020; 14(12):16735-16742. DOI: 10.1021/acsnano.0c04488. View

3.
Hayashi H, Yamaguchi J, Jippo H, Hayashi R, Aratani N, Ohfuchi M . Experimental and Theoretical Investigations of Surface-Assisted Graphene Nanoribbon Synthesis Featuring Carbon-Fluorine Bond Cleavage. ACS Nano. 2017; 11(6):6204-6210. DOI: 10.1021/acsnano.7b02316. View

4.
Ma X, Maier J, Wenzel M, Friedrich A, Steffen A, Marder T . Direct observation of -benzyne formation in photochemical hexadehydro-Diels-Alder (-HDDA) reactions. Chem Sci. 2021; 11(34):9198-9208. PMC: 8163437. DOI: 10.1039/d0sc03184d. View

5.
Bebensee F, Bombis C, Vadapoo S, Cramer J, Besenbacher F, Gothelf K . On-surface azide-alkyne cycloaddition on Cu(111): does it "click" in ultrahigh vacuum?. J Am Chem Soc. 2013; 135(6):2136-9. DOI: 10.1021/ja312303a. View