1609496-70-9Relevant academic research and scientific papers
Comparative study on the reactivity of propargyl and alkynyl sulfides in palladium-catalyzed domino reactions
Castanheiro, Thomas,Schoenfelder, Angèle,Suffert, Jean,Donnard, Morgan,Gulea, Mihaela
, p. 624 - 633 (2017/05/24)
Three types of sulfides bearing a propargyl or an alkynyl moiety have been studied in cyclocarbopalladation/cross-coupling domino palladium-catalyzed sequences. The reactivity of different types of sulfured starting materials has been compared as well as the difference in behavior of these compounds depending on the type of cross coupling ending the domino sequence. It appeared that these cascades were constantly more efficient on the propargyl benzyl thioether. In addition, it has been demonstrated that domino sequences ending with Stille, Suzuki–Miyaura, or Mizoroki–Heck lead efficiently and selectively to the desired cyclized products. Notably, when the introduction of an alkyne is targeted at the end of the cascade, it appeared that the Sonogashira coupling leads every time to the desired cyclic product in the mixture with the product resulting from the direct coupling between the aryl moiety of the substrate and the alkyne used as partner. Finishing the domino sequence with a Stille coupling instead of a Sonogashira one allowed improving significantly the ratio of the mixture in favor of the desired cyclized compound.
Cyclocarbopalladation/cross-coupling cascade reactions in sulfide series: Access to sulfur heterocycles
Castanheiro, Thomas,Donnard, Morgan,Gulea, Mihaela,Suffert, Jean
supporting information, p. 3060 - 3063 (2014/06/23)
Cyclocarbopalladation/cross-coupling cascade reactions were applied for the first time in a sulfur series and represent an efficient route to access sulfur heterocycles. Stille or Suzuki-Miyaura cross-coupling was successfully used as the final reaction.
