An on-surface Diels–Alder reaction

Jesús Castro-Esteban; Florian Albrecht; Shadi Fatayer; Dolores Pérez; Leo Gross; Diego Peña

doi:10.1002/anie.202110311

An on-surface Diels–Alder reaction

Jesús Castro-Esteban, Florian Albrecht, Shadi Fatayer, Dolores Pérez, Leo Gross, Diego Peña

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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.

Original language	English (US)
Pages (from-to)	26346-26350
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	50
DOIs	https://doi.org/10.1002/anie.202110311
State	Published - Dec 6 2021
Externally published	Yes

Bibliographical note

Generated from Scopus record by KAUST IRTS on 2022-09-13

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.202110311

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AU - Castro-Esteban, Jesús

AU - Albrecht, Florian

AU - Fatayer, Shadi

AU - Pérez, Dolores

AU - Gross, Leo

AU - Peña, Diego

N1 - Generated from Scopus record by KAUST IRTS on 2022-09-13

PY - 2021/12/6

Y1 - 2021/12/6

N2 - 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.

AB - 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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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

An on-surface Diels–Alder reaction

Abstract

Bibliographical note

ASJC Scopus subject areas

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