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An on-surface Diels-Alder reaction.

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.

SUBMITTER: Castro-Esteban J

PROVIDER: S-EPMC9298865 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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An on-surface Diels-Alder reaction.

Castro-Esteban Jesús J Albrecht Florian F Fatayer Shadi S Pérez Dolores D Gross Leo L Peña Diego D

Angewandte Chemie (International ed. in English) 20211110 50

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 r ...[more]

PMID: 34664770

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