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We published our new chapter on "Transition Metal‐Catalyzed Reactions with Iodine(III) Reagents" in recent PATAI'S Chemistry of Functional Groups, Hypervalent Halogen Compounds volume. The topic focuses on arylations of aromatic and heteroaromatic systems via C-C bond formations. For further reading, please, Click here.

The most complete resource in functional group chemistry
Patai’s Chemistry of Functional Groups is one of chemistry’s landmark book series in organic chemistry. An indispensible resource for the organic chemist, this is the most comprehensive reference available in functional group chemistry. Founded in 1964 by the late Professor Saul Patai, the aim of Patai’s Chemistry of Functional Groups is to cover all the aspects of the chemistry of an important functional group in each volume, with the emphasis not only on the functional group but on the whole molecule.

The Online Book Series features all the volumes from 1964 to 1995, totalling some 86 classic volumes in print, represented within 83 volumes online (with some volumes merged for the Online Book Series). These are listed below, together with some of the more recent volumes which are available to purchase as part of the electronic major reference work, ePatai. Those books included in the Online Book Series are volumes from 1964 to 1995 (those shown without dates are excluded). All volumes from 1995 onwards (currently 26 volumes) are available as an electronic major reference work, for more information on ePatai, click here.

Each volume contains detailed information on the chemistry of the functional group with the following topics featured in each volume.

General, theoretical and computational aspects of the functional group, for example, quantum chemical treatment, structural and conformational chemistry and thermochemistry.Characterisation and characteristics of the functional groups with chapters covering both qualitative and quantitative methods of determination such as UV, IR, NMR, ESR, PES, RD, CD and mass spectrometry. It will also cover the basicity, acidity or the complex forming ability of the group.

The formation of the functional group and the reactions, transformations and rearrangements which the functional group can undergo, also including synthesis and reaction mechanisms as diverse as photochemistry, radiation chemistry, biochemical formation or classic synthesis and catalysis.

The biological aspects in both biochemistry and molecular biology as well as its application in medicinal chemistry, drug development and drug discovery.

Data and reviews on the important industrial applications in fields such as polymers, materials and nano-materials.Patai’s Chemistry of Functional Groups is much more than just data. It provides detailed insights, review sand overviews on each functional group featured. This depth of content is the strength of the series as well as its broad coverage of techniques, methods, theory and applications.

To download a brochure or find out further information about both the electronic major reference work or take a tour, go to wiley.com/go/patai

Wednesday, 19 December 2018 11:06

Hot Topic: C-C Coupling

Our review entitled "Synthesis of aryl‐ and heteroaryl‐trifluoroethyl ethers: aims, challenges and new methodologies" was highlighted by Wiley Hot Topic: C-C Coupling.

The development of metal-catalyzed cross-coupling reactions over the past 30 years has revolutionized the way, carbon-carbon bonds between sp and sp2 carbon atoms are formed. These methods have profoundly changed the protocols for the construction of natural products, building blocks for supramolecular chemistry and self-assembly, organic materials and polymers, and lead compounds in medicinal chemistry from simpler entities. The 2010 Nobel prize in chemistry for E. Negishi, R. Heck, and A. Suzuki underlines the importance of direct bond formation betweeen carbon atoms. Read articles.

c-c_coupling

Tuesday, 28 August 2018 08:03

OPR&D Picked Up

Our paper entitled "Design of Trifluoroalkenyliodonium salts for Hypervalency Aided Alkenylation‐Cyclization Strategy: Metal‐free Construction of Aziridine Ring" was highlighted by 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.

The efficient construction of small heterocyclic fluorinated building blocks continues to be a major topic of interest for the synthetic community. Novák and co-workers at Eötvös University in Budapest described a new methodology for the synthesis of trifluoromethylated aziridines that expands for the first time the scope of substrates to nonaromatic amines ( Angew. Chem., Int. Ed. 2018, 57, 6643). For that purpose, the authors designed and synthesized trifluoropropenyl iodonium salts as new C2–CF3 synthons. Under the best conditions, dichloromethane as the solvent with 2 equiv of sodium carbonate as the base, an array of substituted alkylamines as well as (hetero)arylamines were converted into trifluoromethylated aziridines in moderate to high yields. An impressive number of functional groups, including alcohols and unprotected anilines, are well-tolerated. DFT calculations were performed to provide insight into the mechanism of the reaction.

Wenyi Zhao, Sylvain Guizzetti, James A. Schwindeman, David S. B. Daniels, Carlos A. Guerrero, David Philip Day, John Knight, Org. Process Res. Dev. 2018, 22, 907-917. DOI: 10.1021/acs.oprd.8b00238 | [Full Text Link]

opprd

Monday, 18 June 2018 12:16

Two New Publications on Pd Catalysis

This June started with two new papers related to palladium cross-coupling reactions.

First, we developed palladium-catalyzed functionalization of aryl- and heteroaryl chlorides with sodium tetrakis-(2-chloroethoxy)-borate salt, which is orthogonal to the simple nucleophilic replacement of the chloro function of the ethylene linker. Palladium Catalyzed Chloroethoxylation of Aromatic and Heteroaromatic Chlorides: an Orthogonal Functionalization of Chloroethoxy Linker. Subsequent amine substitution of the alkyl halide affords 2-aminoethoxy arenes. The paper entitled as "Palladium Catalyzed Chloroethoxylation of Aromatic and Heteroaromatic Chlorides: an Orthogonal Functionalization of Chloroethoxy Linker" and published in Organic & Biomolecular Chemistry (RSC).  For further reading, please, Click here.

 zng pub 66

Second, we disclose a novel catalytic method for the selective deprotection of trimethylsilylacetylenes in Sonogashira reaction. The reagent hexafluorosilicic acid, an inexpensive nontoxic compound, was used to promote the selective desilylation. This paper published by ACS in The Journal of Organic Chemistry as "Catalytic Activation of Trimethylsilylacetylenes: A One-Pot Route to Unsymmetrical Acetylenes and Heterocycles". For further reading, please, Click here.

zng pub 67

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.

zng pub 65 

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.

zng pub 64

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]

oprd

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.

zng pub 62

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.

zng pub 63

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