337974-43-3Relevant academic research and scientific papers
Direct Synthesis of γ-Keto Sulfones from Allylic Alcohols: One-Pot Palladium(II)-Catalyzed Generation of Enones Followed by Water-Mediated 1,4-Addition of Organosulfinates
Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu,Nanubolu, Jagadeesh Babu
, p. 3575 - 3583 (2016/07/28)
Allylic alcohols were exploited as synthetic precursors of γ-keto sulfones. The reaction involved the one-pot generation of α,β-enones in situ from the allylic alcohols by using a PdII–dioxygen catalytic system and subsequent sulfa-Michael addition in the presence of water. Importantly, water was identified as a sustainable substitute for a toxic copper salt to promote organosulfonyl addition. Diverse examples of aromatic and aliphatic γ-keto sulfones were prepared. Specially, Ar–X (X = Br, Cl) bonds were tolerated, which indicated a chemoselective catalytic system for the preparation of halogen-bearing γ-keto sulfones. This one-pot method does not require an acid, a base, or isolation of any intermediate. Control experiments indicated that the active catalyst of the first step also promoted the subsequent C–S bond-formation reaction. Water was found to accelerate the reaction rate and to be involved in the protonolysis of the σ-alkylpalladium complex, as corroborated by deuterium incorporation.
4-[(4'-Methylphenyl)sulfonyl]-1-(trophenylphosphoranylidene)-2-butanone as a New Four-Carbon Synthon for Substituted Divinyl Ketones
Barco, Achille,Benetti, Simonetta,Risi, Carmela De,Marchetti, Paolo,Pollini, Gian Piero,Zanirato, Vinicio
, p. 975 - 986 (2007/10/03)
The title compound and the corresponding anion have been conveniently used as precursors of substituted divinylketones in both carbo- and heterocyclization reactions in one-pot, three-step sequences leading to a wide variety of substituted carbo- and heterocyclic ring systems, as well as to multifunctionalized linear carbon frameworks. The compounds generated through the use of this multi-coupling reagent represent useful synthons for the construction of natural compounds including (+/-)-epibatidine, (-)-anabasine and (+/-)-pyrenophorin.
4-[(4-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2- butanone and its dianion as versatile tools in organic synthesis
Barco, Achille,Benetti, Simonetta,De Risi, Carmela,Marchetti, Paolo,Pollini, Gian P.,Zanirato, Vinicio
, p. 1973 - 1976 (2007/10/03)
The title compound and the corresponding dianion have been used as convenient precursors for substituted divinyl ketones in both carbo- and heterocyclization reactions in a one-pot three-step sequence leading to substituted carbo- and heterocyclic ring systems and for the construction of the 4-keto-2-alkenoate subunit, a common structural feature of a variety of natural compounds, respectively.
