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1.
Chemistry ; 29(33): e202300826, 2023 Jun 13.
Article in English | MEDLINE | ID: mdl-36973187

ABSTRACT

Transition metal-catalyzed divergent synthesis through alternation of the catalyst is appealing, as it provides an operationally simple way to access different valuable products, while using the same reactants as starting materials. Herein, a gold-catalyzed cascade reaction of conjugated diynamides with allylic alcohols is described. By variation of the catalysts, substituted allenes and furans could be obtained selectively. Mechanistic studies indicate that, after the addition of allylic alcohol to gold-activated diynamide, a [3,3]-sigmatropic rearrangement would take place and lead to the formation of a common reactive intermediate, which would further convert to the final products selectively. Further variation of the structure of diynamides has unveiled an additional reaction sequence involving intramolecular Himbert arene/allene Diels-Alder cycloaddition to afford a series of dearomatized products bearing bicyclo[2,2,2]octadiene core.


Subject(s)
Gold , Propanols , Gold/chemistry , Catalysis
2.
Org Lett ; 24(23): 4298-4303, 2022 Jun 17.
Article in English | MEDLINE | ID: mdl-35666892

ABSTRACT

Catalytic dearomatization has been considered as a valuable approach to convert readily accessible flat molecules to products with three-dimensional frameworks. Herein, an unprecedented gold-catalyzed oxidative Büchner-type cyclopropanation is described that enables the cycloisomerization of diynamides. By variation of the position of substituents on the phenyl ring, a variety of fused N-heterocyclic products with challenging structural skeletons were obtained divergently.

3.
Angew Chem Int Ed Engl ; 59(41): 18261-18266, 2020 10 05.
Article in English | MEDLINE | ID: mdl-32619036

ABSTRACT

Tricyclic ring systems possessing a dibenzo structure joined to a seven-membered heterocyclic ring frequently show important biological activities. However, a modular approach to these molecules based on efficient intermolecular reaction of readily available chemicals is lacking. Herein, an unprecedented palladium-catalyzed formal [4+3] annulation for modular construction of these tricyclic systems is described. This reaction features easily accessible reactants (o-haloarylaldehydes and N-tosylhydrazones), broad substrate scope, and excellent functional group compatibility. The synthetic potential is demonstrated by the easy scale-up reactions, late-stage modification of complex molecules, and collective synthesis of bioactive molecules and approved drugs.

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