2024
DOI: 10.1021/acs.orglett.3c04339
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Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes

Zhen-Hua Wang,
Xiao-Hui Fu,
Qun Li
et al.

Abstract: This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence of a diphosphine ligand, the reaction proceeds via a (5+2) cycloaddition pathway to afford 1,3-diazepin-4-ones in excellent yields, while using a monophosphine ligand, the reaction proceeds smoothly via a (3+2) cycloaddition pathway to give imidazolidin-4ones in good yields.

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Cited by 8 publications
(2 citation statements)
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“…S1†) 50 via the ring opening of epoxide as depicted in Scheme 6c. Later it was found that SnCl 2 is not necessary for the formation of 6 (Scheme 6b), 51 but rather, its absence inhibits the formation of 7 (Scheme 6f). Therefore, it is worth mentioning that SnCl 2 plays a crucial role in activating styrene oxide.…”
Section: Resultsmentioning
confidence: 99%
“…S1†) 50 via the ring opening of epoxide as depicted in Scheme 6c. Later it was found that SnCl 2 is not necessary for the formation of 6 (Scheme 6b), 51 but rather, its absence inhibits the formation of 7 (Scheme 6f). Therefore, it is worth mentioning that SnCl 2 plays a crucial role in activating styrene oxide.…”
Section: Resultsmentioning
confidence: 99%
“…In the past decades, the palladium-catalyzed cycloaddition reaction has become one of the most powerful and efficient methods to construct carbo- and heterocyclic frameworks . Various cycloaddition reactions via allylpalladium intermediates have been developed for the synthesis of cyclic compounds. Numerous dipolarophiles, such as electron-deficient alkenes, imines, aldehydes, and 1,3-diploes, have been applied in palladium-catalyzed cycloaddition reactions. As a type of readily accessible compound, sulfur ylides have also been successfully used in Pd-catalyzed cycloaddition reactions because of their intrinsic nucleophilic and electrophilic properties.…”
mentioning
confidence: 99%