14070-60-1Relevant academic research and scientific papers
Synthesis and Photocatalytic Reactivity of Vinylsulfonium Ylides
Klose, Immo,Misale, Antonio,Maulide, Nuno
, p. 7201 - 7210 (2016)
Although sulfur ylides are textbook reagents in organic synthesis, surprisingly little variation of substituents on sulfur is usually observed. In particular, vinylsulfonium ylides have been neglected so far. Herein, we present a study on their synthesis and reactivity, including interesting behavior under photocatalytic conditions.
Gold-catalyzed intermolecular synthesis of alkylidenecyclopropanes through catalytic allene activation
Sabbatani, Juliette,Huang, Xueliang,Veiros, Luis F.,Maulide, Nuno
supporting information, p. 10636 - 10639 (2014/09/17)
A stereoselective gold(I)-catalyzed intermolecular cyclopropanation of allenamides with stabilized sulfonium ylides is reported. This transformation enables the direct synthesis of diacceptor alkylidenecyclopropanes and proceeds under very mild conditions through allene activation. Three is my lucky number: A mild stereoselective gold(I)-catalyzed intermolecular cyclopropanation of allenamides with stabilized sulfonium ylides is reported. This transformation delivers diacceptor alkylidenecyclopropanes and unusually proceeds through allene activation rather than by metallocarbene formation (see scheme, EWG=electron-withdrawing group).
Sulfur(IV)-mediated transformations: From ylide transfer to metal-free arylation of carbonyl compounds
Huang, Xueliang,Patil, Mahendra,Fares, Christophe,Thiel, Walter,Maulide, Nuno
supporting information, p. 7312 - 7323 (2013/06/26)
The development of a direct ylide transfer to carbonyl derivatives and of a sulfoxide-mediated arylation is presented from a unified perspective. Mechanistic studies (including density functional calculations) support a common reaction pathway and showcase how subtle changes in reactant properties can lead to disparate and seemingly unrelated reaction outcomes.
A direct ylide transfer to carbonyl derivatives and heteroaromatic compounds
Huang, Xueliang,Goddard, Richard,Maulide, Nuno
supporting information; experimental part, p. 8979 - 8983 (2011/02/24)
Power transfer: The title reaction proceeds under mild conditions (room temperature, short reaction times) and directly affords sulfonium ylides from active methylene compounds and heteroaromatics in a single step and in high yields. A detailed comparative structural analysis of a variety of ylides is presented and the implications of structure on the reactivity of these compounds are discussed.
