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Lewis Acid-Catalyzed Diels-Alder Reactions: Reactivity Trends across the Periodic Table.

ABSTRACT: The catalytic effect of various weakly interacting Lewis acids (LAs) across the periodic table, based on hydrogen (Group 1), pnictogen (Group 15), chalcogen (Group 16), and halogen (Group 17) bonds, on the Diels-Alder cycloaddition reaction between 1,3-butadiene and methyl acrylate was studied quantum chemically by using relativistic density functional theory. Weakly interacting LAs accelerate the Diels-Alder reaction by lowering the reaction barrier up to 3 kcal mol^-1 compared to the uncatalyzed reaction. The reaction barriers systematically increase from halogen

SUBMITTER: Vermeeren P

PROVIDER: S-EPMC8360170 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Lewis Acid-Catalyzed Diels-Alder Reactions: Reactivity Trends across the Periodic Table.

Vermeeren Pascal P Tiezza Marco Dalla MD van Dongen Michelle M Fernández Israel I Bickelhaupt F Matthias FM Hamlin Trevor A TA

Chemistry (Weinheim an der Bergstrasse, Germany) 20210501 41

The catalytic effect of various weakly interacting Lewis acids (LAs) across the periodic table, based on hydrogen (Group 1), pnictogen (Group 15), chalcogen (Group 16), and halogen (Group 17) bonds, on the Diels-Alder cycloaddition reaction between 1,3-butadiene and methyl acrylate was studied quantum chemically by using relativistic density functional theory. Weakly interacting LAs accelerate the Diels-Alder reaction by lowering the reaction barrier up to 3 kcal mol<sup>-1</sup> compared to the ...[more]

PMID: 33780068

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