Supramolecular “baking powder”: a hexameric halogen-bonded phosphonium salt cage encapsulates and functionalises small-molecule carbonyl compounds

文献情報

出版日 2023-11-28

DOI 10.1039/D2SC04615F

インパクトファクター 9.825

著者

Hatem M. Titi, Yong Teoh

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要旨

We report a hexameric supramolecular cage assembled from the components of a Wittig-type phosphonium salt, held together by charge-assisted halogen bonds. The cage reliably encapsulates small polar molecules, including aldehydes and ketones, to provide host–guest systems where components are pre-formulated in a near-ideal stoichiometry for a mechanochemical base-activated Wittig olefination. These pre-formulated solids represent a proof-of-principle for a previously not reported supramolecular design of solid-state reactivity in which the host for molecular inclusion also acts as a complementary reagent for the subsequent chemical transformation of an array of guests. The host–guest solid-state complexes can act as supramolecular surrogates to their Wittig olefination vinylbromide products in a Sonogashira-type coupling that enables one-pot mechanochemical conversion of an aldehyde to an enediyne.

掲載誌

Chemical Science

CiteScore: 14.4

自己引用率: 3.9%

年間論文数: 1413

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Supramolecular “baking powder”: a hexameric halogen-bonded phosphonium salt cage encapsulates and functionalises small-molecule carbonyl compounds

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