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2018

Design of Trifluoroalkenyliodonium salts for Hypervalency Aided Alkenylation‐Cyclization Strategy: Metal‐free Construction of Aziridine Ring, Ádám Mészáros, Anna Székely, András Stirling, Zoltán Novák, Angew. Chem. Int. Ed. 2018, 57, 6643-6647. DOI: 10.1002/anie.201802347 | [Full Text Link] [Supp. Info. Link]

Synthesis of fluorinated compounds and their use as pharmaceutical ingredients or synthetic building blocks are in the focus of chemical and medicinal research. However, the efficient synthesis of trifluoromethylated nitrogen heterocycles sometimes are challenging. Herein, we disclose a simple aziridination process which relies on the use of amines and novel alkenyl synthon for the access of trifluoromethylated strained heterocycle. With the utilization of a newly designed, bench stable but highly reactive hypervalent alkenyl iodonium species, the three membered heterocyclic ring can be constructed from simple amines without structural limitation with high efficiency under mild conditions in the absence of transition metal catalysts. The special reactivity of the new trifluoropropenyl synthon toward nucleophilic centres could be exploited in more general cyclization and alkenylation reactions in the future.

 zng pub 65

Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas, Dániel Cs. Simkó, Péter Elekes, Vivien Pázmándi, Zoltán Novák, Org. Lett2018, 20, 676-679. DOI: 10.1021/acs.orglett.7b03813 | [Full Text Link] [Supp. Info. Link]

A novel method for the ortho alkylation of acetanilide and aromatic urea derivatives via C–H activation was developed. Alkyl dibenzothiophenium salts are considered to be new reagents for the palladium-catalyzed C–H activation reaction, which enables the transfer of methyl and other alkyl groups from the sulfonium salt to the aniline derivatives under mild catalytic conditions.

zng pub 64