Annalen der Pharmacie

Abstract Trifluoromethyl ynones derived from the refrigerant gas HFO‐1234yf (2,3,3,3‐tetrafluoropropene) react with nucleophiles via a Michael‐type addition process and the allenolate intermediate formed reacts intramolecularly with a carbonyl group to form heterocyclic derivatives. Thus, reaction of 2‐amino and 2‐hydroxyl benzaldehyde or ketone substrates with trifluoromethyl ynone derivatives gives trifluoromethyl quinoline and chromene products by a one‐pot tandem ring closing sequence, forming pharmaceutically relevant structures from an inexpensive starting material without the need for transition metals or column chromatography. The 2‐trifluoromethylquinoline products also show unusual fluxional behaviour, which was explored through 2‐D NMR and X‐ray crystallographic studies.

Thomas G. F. Marsh

Alessia Santambrogio

Ben J. Murray

Lee T. Boulton

Juan A. Aguilar

Dmitry S. Yufit

Graham Sandford

William D. G. Brittain

European Journal of Organic Chemistry

HFO‐1234yf as a CF3 Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones

Dynamic combinatorial chemistry (DCC) is a powerful tool to identify bioactive compounds. This efficient technique allows the target to select its own binders and circumvents the need for synthesis and biochemical evaluation of all individual derivatives. An ever‐increasing number of publications report the use of DCC on biologically relevant target proteins. This minireview complements previous reviews by focusing on the experimental protocol and giving detailed examples of essential steps and factors that need to be considered, such as protein stability, buffer composition and cosolvents.

Alwin M. Hartman

Robin M. Gierse

Anna K. H. Hirsch

Protein‐Templated Dynamic Combinatorial Chemistry: Brief Overview and Experimental Protocol

Abstract Piperazines are widely used as central elements in the construction of bioactive molecules. Herein, the short synthesis of two chiral 2,6‐bridged piperazines possessing orthogonally stable protecting groups from readily available starting materials is described. It is suggested that these molecules may be used as conformationally restricted scaffolds for the combinatorial synthesis of drug‐like compounds. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)

Till Opatz

Synthesis of two Conformationally Restricted Piperazine Scaffolds for Combinatorial Chemistry

两种构象限制性哌嗪骨架的合成用于组合化学

Recently the aqueous medium has attracted the interest of organic chemists, and many, sometimes surprising, discoveries have been made. Among the organic reactions investigated in aqueous medium, the Diels−Alder cycloaddition has been the most widely studied because of its great importance in the synthetic and theoretical fields. The Diels−Alder reaction is greatly enhanced by Lewis acid catalysis, and this review illustrates recent significant results in this field when the reaction is performed in aqueous medium.

Francesco Fringuelli

Oriana Piermatti

Ferdinando Pizzo

Luigi Vaccaro

Recent Advances in Lewis Acid Catalyzed Diels−Alder Reactions in Aqueous Media

路易斯酸催化水介质中Diels−Alder反应的最新进展

Abstract The three carbasugars, 5a‐carba‐α‐ D ‐gluco‐, ‐α‐ D ‐galacto and ‐β‐ L ‐gulopyranose pentaacetates 42 , 35 and 28 respectively, have been prepared in a stereodivergent manner from D ‐mannose. Alkynyl derivatives of 2,3:4,6‐di‐ O ‐isopropylidene‐ D ‐mannopyranose, which are homologated at C‐1 by reaction with trimethylsilylacetylide, undergo a 6‐ exo ‐ dig radical cyclization, from a radical located at C‐5, to yield a mixture of highly functionalized exo‐methylenecyclohexanes. Ozonolysis of the exocyclic double bond in the latter generated cyclohexanones which, upon stereoselective reduction of the carbonyl moiety followed by site‐selective deoxygenation either at position C‐4 or C‐5a (parent carbohydrate numbering), afforded the title carbasugars. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)

Ana M. Gómez

Eduardo Moreno

Serafín Valverde

J. Cristóbal López

A Stereodivergent Approach to 5a‐Carba‐α‐<scp>D</scp>‐gluco‐, ‐α‐<scp>D</scp>‐galacto and ‐β‐<scp>L</scp>‐gulopyranose Pentaacetates from <scp>D</scp>‐Mannose, Based on 6‐exo‐dig Radical Cyclization and Barton−McCombie Radical Deoxygenation

一种基于6-exo-dig自由基环化和Barton-McCombie自由基脱氧的立体发散方法，从D-甘露糖合成5a-碳-α-D-吡喃葡糖、-α-D-吡喃半乳糖和-β-L-吡喃古洛糖五乙酸酯

Plastics play a crucial role in the survival and advancement of human civilization. However, the increasing challenge of plastic pollution presents significant obstacles. Disposal methods such as incineration and landfilling result in substantial resource wastage and pose potential environmental hazards. The slow progress in recycling and reusing waste plastics hinders their industrial application and effective response to environmental crises. Photocatalysis offers promising solutions for the future of plastic recycling, particularly with the recent increase in photocatalytic degradation methods for polystyrene (PS). This review provides a comprehensive overview of the latest advancements in the photooxidation of PS into high‐value chemicals.

Shusheng Jiang

Yunhan Chen

Yahao Huang

Peng Hu

Photooxidation of Polystyrene into High‐Value Chemicals

聚苯乙烯光氧化转化为高价值化学品

Chalcogen bond catalysis is a promising catalytic strategy, characterized by its environmental friendliness, relatively inexpensive cost, and similar reactivity to transition metal catalysis. Experimental results suggest that the S•••π and Se•••π bonds can efficiently drive the vinyl‐indole‐based Diels‐Alder reaction (Angew. Chem. Int. Ed. 2021, 60, 9395‐9400). In this work, chalcogen bond catalysis in the Diels‐Alder reaction between 2‐vinylindoles has been investigated based on density functional theory. For this reaction, the Te•••π bond catalysis is as an alternative catalytic strategy. The Diels‐Alder reaction catalyzed by chalcogen bond is stepwise and involves two steps: the carbon–carbon bond formation process and the cyclization process. The cyclization process is the rate‐determining step. From the perspective of energy decomposition analysis, the electrostatic interaction is the main factor to cause Se•••π bond catalysis, the polarization interaction is the main factor to cause Te•••π bond catalysis. Additionally, this catalytic reaction involves the endo pathway and exo pathway. The Gibbs free energy barrier values of the endo pathway are lower than those of the exo pathway, which facilitates the formation of the endo product. This study will provide a valuable perspective on the application of chalcogen bond in the activation of alkenes.

Chang Zhao

Mengmeng Wang

Yanli Zeng

Activation of Alkenes via Chalcogen Bond: Chalcogen•••π Bond Catalyzed the Diels‐Alder Reaction of 2‐Vinylindoles

通过硫属元素键活化烯烃：硫属元素•••π键催化2-乙烯基吲哚的狄尔斯-阿尔德反应

The methylthio group plays a significant role in antitumor bioactive molecules, candidate drugs and natural products. Deuteration modification of drugs, which could prolong the half‐life, reduce toxicity, and enhance targeting, has become an important strategy in the development and discovery of innovative drugs. Combining the unique properties of the methylthio group with the deuteration effect, the rapid introduction of trideuteromethylthiol groups into small organic molecules is essential for advancing the research and development of deuterated drugs. With the rapid development of new trideuteromethylthiolation reagents, this review first outlines the indirect introduction of trideuteromethylthiol groups, and then discusses the direct nucleophilic, electrophilic and free radical trideuteromethylthiolation methods.

Ge Wu

Kemeng Zhang

Yunfei Ma

Lin Zhao

Xinyu Zhou

Recent Advances in the Synthesis of Trideuteromethyl Sulfide

三甲基硫醚合成研究的最新进展

Furfural is produced on a large commercial scale from lignocellulose and can be used for the preparation of several industrial chemicals with four to five carbon atoms. Further functionalization of furfural by C−H activation, however, is less widely developed. In the present work, tetrabutylammonium decatungstate is investigated as an inexpensive photocatalyst for activating the aldehyde C−H bond and mediate a coupling between furfural and electron‐deficient olefins. The results show that furfural can be successfully added to benzylidene malononitriles, acrylates, itaconic anhydride, maleic anhydride, 2‐vinylpyridine and phenyl vinyl sulfone to generate the corresponding furanyl ketones in moderate‐to‐good yields. The electronic properties of the electron‐deficient olefins are instrumental for achieving a favorable reaction with furfural. The findings show how photocatalysis can be used to form new carbon‐carbon bonds from a platform molecule, which in this way can be converted into a number of more advanced structures.

Emil Krogh Nielsen

Kassem El‐Chami

Clara Mondrup de Lichtenberg

Robert Madsen

Eur J Org Chem

Decatungstate‐Catalyzed Carbon‐Carbon Bond Formation Between Furfural and Electron‐Deficient Olefins

十钨酸盐催化糠醛与缺电子烯烃的碳-碳键形成

Abstract Lignocellulosic biomass remains underutilized despite its annual production in gigaton quantities. Sulfur is another vastly underutilized waste product of fossil fuel refining. New mechanistic insight into the reactions of sulfur unveiled since 2020 suggest a rich and hitherto unexplored chemistry between biomass‐derived olefins and elemental sulfur. In this study, four biomass‐derived olefins (eugenol ( 1 ), 4‐allyl‐2,6‐dimethoxyphenol ( 2 ), o ‐eugenol ( 3 ), and 2‐allyl‐6‐methylphenol (4) ) were reacted with elemental sulfur to elucidate the S−C bond‐forming and other reactivity of these compounds. Each of the compounds was reacted with elemental sulfur in three sulfur : organic reactant ratios (2 : 1, 4 : 1 and 9 : 1) and at two temperatures (180 °C or 230 °C). Product mixtures were characterized using 1 H NMR spectrometry and GC‐MS analysis. Products resulting from a range of mechanisms were unveiled, including inverse vulcanization, S−C allylic/benzylic bond formation, S−C aryl bond formation, intramolecular cyclization, C−C σ‐bond scission, and C−O σ‐bond scission. It is anticipated that the insights from this study will support further synergy between the critical sustainability goals of biomass and sulfur utilization.

Nawoda L. Kapuge Dona

Charini P. Maladeniya

Rhett C. Smith

Reactivity of Biomass‐Derived Olefins with Elemental Sulfur: Mechanistic Insight

生物质衍生烯烃与元素硫的反应性：机理探究

短名	Eur J Org Chem
Journal Impact	2.69
国际分区	CHEMISTRY, ORGANIC(Q2)
期刊索引	SCI Q2中科院 3 区

ISSN	0365-5490, 1099-0690, 1434-193X
h-index	173
国内分区	化学(3区)化学有机化学(3区)

出版信息	出版商: John Wiley and Sons Ltd，出版周期: ，期刊类型: journal，开源期刊: 否
基本数据	创刊年份: 1832，原创研究文献占比: ，自引率:， Gold OA占比:

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HFO‐1234yf as a CF₃ Building Block: Synthesis of Trifluoromethyl Quinoline and Chromene Derivatives from Trifluoromethyl‐ynones