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A new route has been discovered to obtain CF3 substituated N-aryl, alkyl and tosylaziridine products. 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 paper entitled as "Design of Trifluoroalkenyliodonium salts for Hypervalency Aided Alkenylation‐Cyclization Strategy: Metal‐free Construction of Aziridine Ring" and published in Angewandte Chemie International Edition (Wiley). For further reading, please, Click here.

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C−C bond-forming reactions via aromatic C−H bond activation processes have been studied in this paper. C−H activation based direct alkylations by alkyl group transfer are less explored in this field. However, the introduction of alkyl groups into aromatic systems, especially the ubiquitous methyl group in molecular scaffolds, could have beneficial effects on biological properties. This paper describes "Sulfonium Salts as Alkylating Agents for Palladium-Catalyzed Direct Ortho Alkylation of Anilides and Aromatic Ureas" presented by Dániel Simkó et. al. in Organic Letters (ACS). For further reading, please, Click here.

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Monday, 11 December 2017 12:38

OPR&D Highlights

Our new publication entitled "Palladium Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of Trifluoro Analog of Sildenafil" had been picked up by the Highlights of OPR&D! The highlights are selected by a group of industrial chemists as a service to the readership who has a strong interest in practical chemistry that addresses and solves industrial questions.These trifluoroethoxylated compounds are both very useful and not always that easy to produce.

Wenyi Zhao, Dongbo Zhao, Sylvain Guizzetti, James A. Schwindeman, David S. B. Daniels, Carlos A. Guerrero, Arjun Raghuraman, John Knight, Org. Process Res. Dev. 2017, 21, 1873-1883. DOI: 10.1021/acs.oprd.7b00371 | [Full Text Link]


Sunday, 10 September 2017 14:57

September starts with two new publications

We are pleased to share our new papers.

Aradi K. and her co-workers presented a mild N-arylation of nitroenamine derivatives utilizing diaryliodonium triflates and copper(I) chloride as a catalyst. For further reading, please, click here.

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Pethő B. and his co-workers developed a synthetic method for 2,2,2-trifluoroethoxylation of aromatic and heteroaromatic chlorides utilizing borate salt. Under palladium catalyzed reaction conditions an additional analog of Sildenafil was synthetized also. The paper was published in Chemistry - A European Journal (Wiley).For further reading, please, click here.

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Our group was presented a new syhtetic method for the desilylation of silylacetylenes via aquaous solution of hexafluorosilicic acid. The applicability of the novel, cheap and environmentally friendly reagent was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot reactions. This paper has been published in Synthesis (Thieme) and entitled as "Hexafluorosilicic Acid as a Novel Reagent for the Desilylation of Silylacetylenes: Application in Sequential Sonogashira Coupling and Click Reaction". For further reading, please, click here.

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 The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot
Saturday, 04 February 2017 14:12

Synthesis of Azulenes in Organic Letters

Our new paper has been published in topic of azulene chemistry, in Organic Letters (ACS)! This paper entitled as "Gold-Catalyzed Direct Alkynylation of Azulenes" and contains 18 examples of novel TIPS-acetilene-azulenes. For further reading please, Click Here.

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The groups last publication has been accepted for publication in European Journal of Organic Chemistry (Wiley). This project was entitled as "Erythrosine B catalyzed visible-light photoredox arylation-cyclization of N-alkyl-N-aryl-2-(trifluoromethyl)acrylamides to 3-(trifluoromethyl)indolin-2-one derivatives" and presented by Zsombor Gonda, Ferenc Béke, Orsolya Tischler, Milán Petró, Zoltán Novák and Balázs Tóth. In this work, the novel erythrosine B organic sensitizer dye was utilized as photocatalyst to cyclize the trifluoroacrylamides. You can read this paper already in Accepted Articles section at Wiley. For further reading please, Click Here.

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Our new publication was accepted in Advanced Synthesis & Catalysis (Wiley). This paper is about "Direct ortho-Trifluoroethylation of Aromatic Ureas by Palladium Catalyzed C-H activation: A Missing Piece of Aromatic Substitutions" and released yesterday (15.12.2016).  The authors, Szabolcs Kovács, Balázs L. Tóth, Gábor Borsik, Tamás Bihari, Nóra V. May, András Stirling and Zoltán Novák reported a easily feasible method for trifluoroethylation, which was unprecedented transformation considering the direct alkylation of ureas.

Abstract: Development of direct late-stage installation of alkyl groups into aromatic systems is an important and challenging task of current organic chemistry. In spite of the existing functionalization methods in organic chemistry for the substitution reactions on aromatic systems, the direct alkylation of aromatic ureas is unknown. Herein, as a first example we report a novel palladium catalyzed fluoroalkylation process by C−H activation for the access of ortho trifluoroethylated aromatic ureas. The application of novel, highly active trifluoroethyl(mesityl)iodonium salt enables the efficient introduction of the trifluoroethyl group at 25 °C in 3 hours in high yields (up to 95%) with good functional group tolerance. DFT calculations have revealed a rate determining oxidative alkyl-group transfer preceded by an unexpected C−H activation route on the Pd center during the catalytic cycle, where the deprotonation is assisted by an external triflate anion. For further reading please, Click Here. DOI: 10.1002/adsc.201601136

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