Abstract Quantum chemical calculations are mainly regarded as a method for mechanistic studies in organic chemistry, whereas their use the simulation of unknown reactions could greatly assist reaction development. Here we report strategy developing multicomponent on basis results computational simulations. In silico screening with difluorocarbene using artificial force induced suggested that cy...

The efficient synthesis of aN-benzoyliminoimidazolium ylide provides access to a new type of N-hetereocyclic anionic carbene, from which air stable Ag(I) and Cu(II) complexes and a catalytically active Rh(I) complex were formed.

The total synthesis of 8a-epi-swainsonine has been achieved in 20% overall yield from R-glyceraldehyde dimethylacetonide 3 through epoxidation with the achiral furyl-substituted sulfonium ylide 2d as one of the key steps.

The bond dissociation enthalpies (BDEs) of sulfur and selenium ylides have been estimated by applying MP2/6-311++G(3df,2p)//MP2/6-31G(d,p), G3, and other computational methods. Computed sulfoxide bond enthalpies were compared to experimental results to ensure the reliability of the computational methods before extending to related compounds. The examined ylides include the following: sulfoxides...

Herein, we describe a novel approach for the practical synthesis of tetrasubstituted thiophenes 8. The developed method was particularly used for the facile preparation of thienyl heterocycles 8. The mechanism for this reaction is based on the formation of a sulfur ylide-like intermediate. It was clearly suggested by (i) the intramolecular cyclization of ketene N,S-acetals 7 to the correspondin...

Abstract This invited Team Profile was created by the Gessner and Gooßen research groups at Ruhr-University Bochum (Germany). They recently published a series of articles in Angewandte Chemie on application ylide-substituted phosphines (YPhos) palladium-catalyzed coupling reactions. Owing to their inherently strong sigma-donating ability modular synthesis, YPhos ligands can be tailored fit dema...

On the basis of ab initio calculations we propose a revised mechanism for the reaction of organic sulfides with singlet oxygen, which is more consistent with experimental evidence than previous schemes. In aprotic solvents the reagents initially form a weakly bound peroxysulfoxide, with a small barrier due to entropy. The peroxysulfoxide may decay back to ground state (triplet) oxygen, be trapp...

UNLABELLED Translation of new methodologies for labeling nonactivated aromatic molecules with (18)F remains a challenge. Here, we report a one-step, regioselective, metal-free (18)F-labeling method that uses a hypervalent iodonium(III) ylide precursor, to prepare the radiopharmaceutical (18)F-3-fluoro-5-[(pyridin-3-yl)ethynyl]benzonitrile ((18)F-FPEB). METHODS Automated radiosynthesis of (18)...

The reaction of readily available imidazolium–phosphonium salt [MesIm(CH2)3PPh3](OTf)2 with PdCl2 in the presence an excess Cs2CO3 afforded selectively one step cationic Pd(II) complex [(C,C,C)Pd(NCMe)](OTf) exhibiting LX2-type NHC-ylide-aryl C,C,C-pincer ligand via formal triple C–H bond activation. replacement labile MeCN latter by CNtBu and CO fragments allowed to estimate overall electronic...