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Brønsted Acid Catalyzed Dehydroxylative Cyanation of Benzylic Alcohols with Trimethylsilyl Cyanide Using 1,1,1,3,3,3-Hexafluoro-2-propanol as a Solvent Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-07 Kosho Makino, Mai Hasebe, Shunsuke Sueki, Masahiro Anada
A concise and direct cyanation of secondary and tertiary benzylic and allylic alcohols catalyzed by Brønsted acid has been developed using trimethylsilyl cyanide (TMSCN) as a cyanide source and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a solvent. The present transition metal-free catalytic process is operationally simple to perform under “open-flask” conditions and it is applicable to the preparation
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Potassium tert-Butoxide-Promoted Aerobic Dehydrazination of Arylhydrazines: From Arylhydrazines to Substituent Aromatics Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-06 Shengli Zhang, Xiangdong Tan, Yingxu Wu, Yu Si, Rensong Sun, Ziang Liu, Yun Nie, Zhigang Gao, Lei Wang
An efficiently aerobic dehydrazination of arylhydrazines promoted by potassium tert-butoxide (tBuOK) is detailed in this study. This method smoothly produces aromatics analogues from arylhydrazines using catalytic amount of tBuOK under practical conditions, exhibiting excellent functional group tolerance and a broad substrate scope. The application potential of this approach is further demonstrated
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Synthesis of 1,4-Disubstituted and 1-Substituted β-Carbolines via 3-Substituted 2-Acylindoles Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-07 Katharina Thees, Martin Untergehrer, Ilya A. P. Jourjine, Franz Bracher
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Construction of C5‐Indole Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed β‐C(sp3)‐H Functionalization Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-04 Pooja Patel, Srinivasarao Arulananda Babu, Radha Tomar
We report the construction of C5‐indole unnatural amino acid derivatives via the diastereoselective Pd(II)‐catalyzed prochiral β‐C(sp3)‐H arylation of racemic (DL), and enantiopure L‐ and D‐carboxamides of amino acids with 5‐iodoindoles. Independently, indole‐based compounds and amino acid motifs are important small molecules in organic synthesis and drug discovery research. This report aimed to contribute
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Synthesis and Optical Property Modulation of Substituted [2.2]Paracylophanes through Through‐Space Conjugation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-04 Sushil Lambud, Anil Bhadke, Zahir Ali Siddiqui, Vaishali Chaudhari, Nagaiyan Sekar, Rajesh Bhosale, Sandeep More
4,16‐para‐substituted [2.2]paracylophane with naphthalene (PCP⎼NAP), anthracene (PCP⎼ANTH), and tetraphenylethylene (PCP⎼TPE), as new through‐space conjugated dimers, were prepared by the Suzuki–Miyaura cross‐coupling reaction of 4,16‐diboryl[2.2]paracyclophane and the corresponding bromo derivative using Pd(PPh3)4 as a catalyst and KOH as a base. The synthesized compounds were fully characterized
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Daphnicyclidin Alkaloids 2001‒2023 Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-03 Martin Hiersemann, Jan Gierok
The Daphniphyllum alkaloids represent a particularly diverse class of complex diterpene alkaloids, which are characterized by their enormous structural diversity. The daphnicyclidins, a subgroup of these alkaloids, stand out due to their unique pentafulvene structural motif. This review article gives an overview of the compounds that have been isolated so far and can be assigned to this subgroup. Furthermore
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Diastereoselective Aldol Reaction of α‐Azido Ketones with α‐CF3 Pyruvate to Organoazides with Vicinal Tetrasubstituted Carbons Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-03 Yang Gao, Xue-Xin Zhang, Zhi Tu, Jin-Sheng Yu, Jian Zhou
A direct diastereoselective aldol reaction of cyclic or acyclic α‐azido ketones with α‐trifluoromethyl (CF3) pyruvate catalysed by DABCO is developed, which allowed the facile access of CF3‐containing multifunctional organoazides with vicinal tetrasubstituted carbons in good to high yields and diastereoselectivities. Moreover, phenylethynyl trifluoro‐ and difluoromethyl ketones are also viable substrates
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Supramolecular Chemistry: Exploring the Use of Electronic Structure, Molecular Dynamics, and Machine Learning Approaches Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-03 Matheus C. Colaço, Vinícius A. Glitz, Amanda K. Jacobs, Vinicius Capriles Port, Giovanni Finoto Caramori
This review aims to highlight the role that computational chemistry has played in advancing the supramolecular chemistry field. We demonstrated recent uses of computational methodologies to elucidate noncovalent interactions in various processes occurring in supramolecular systems. We also emphasized the contributions of these techniques to studying reactions within confined space, showing how computational
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Electrochemical Decarboxylative Addition of N‐Aryl Glycines to Enaminones: Access to C3‐Aminomethyl Chromones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-01 Siyang Han, Chengcheng Fang, Yaoge Zhang, Sifeng Li, Min Huang, Taimin Wang, Baigang An, Bin Cheng
An electrochemical decarboxylative addition of N‐substituted glycines to enaminones has been developed and conducted under oxidant‐, catalyst‐, and light‐free conditions in acetonitrile at room temperature by using electron as the traceless oxidant, which provided a green approach to C3‐aminomethyl chromones. The resulting products were formed through radical addition/oxidation/cyclization or electrophilic
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Electrocatalytic Hydrogen Evolution Reaction Enabling Cyanation of Electron‐poor Carbons with Acetone Cyanohydrin Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-01 Valerio Morlacci, Caterina Momoli, Meklind Ndrita, Massimiliano Aschi, Antonio Arcadi, Laura Palombi
The Pt‐cathode hydrogen evolution reaction (Pt‐HER) of acetone cyanohydrin provides an alternative method for introducing the cyano group onto electrophilic carbons of imines and chalcones. The synthesis of α‐aminonitriles and β‐cyano ketones has been achieved smoothly with a small excess of cyanating agent (2 equivalent), catalytic amount of supporting electrolyte and low electricity consumption (0
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The Environmental Pollutant NO3• Rapidly Damages Alkene Moieties in Lipids Through Electron Transfer Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-05-01 Yu-Chen Chiu, Uta Wille, Joses G. Nathanael
The presence of alkene moieties in fatty acids of (phospho)lipids and cholesterol derivatives makes them highly susceptible to damage by nitrate radicals (NO3•), potentially formed through simultaneous exposure to the environmental air pollutants nitrogen dioxide (NO2•) and ozone (O3). Absolute rate coefficients derived from reactions with simplified model systems range from 4 to 8 × 109 M−1 s−1 in
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Diaminomaleonitrile – Mono‐, Di‐ …and Tetraprotonation?! Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-30 Alexander Nitzer, Pauline Manhart, Christoph Jessen, Andreas J. Kornath
The successful mono‐ and diprotonation of DAMN showed the first site of protonation to be an amino group, while the second protonation occurs at a nitrile group. The prepared salts were characterized by vibrational spectroscopy and single crystal X‐ray crystallography. Under strong superacidic conditions and with sufficient time cyclization of two (di)protonated molecules of DAMN is observed, yielding
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2‐Methylene‐1,2‐dihydropyridines (2‐pyNHOs): Highly Nucleophilic Enamines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-30 Annika Behnke, Andreas Eitzinger, Yijie He, Patrick W. Antoni, Armin R. Ofial, Max M. Hansmann
The high reactivity of 2‐methylene‐1,2‐dihydropyridines also known as 2‐methylpyridinium derived N‐heterocyclic olefins (2‐pyNHOs) has been recognized in organic synthesis, yet a quantification of their nucleophilicity is lacking. Herein we used stopped‐flow photometry to determine the nucleophilicity of a series of 2‐pyNHOs from the kinetics of their reactions with quinone methides and benzhydrylium
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Total Synthesis of the Naturally Occurring Cyclic Tetrapeptide JM‐47 and Analogues through Late‐Stage Functionalization of a Common Scaffold Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-30 Rajat Ghosh, Shital K Chattopadhyay
A unified approach to access the naturally occurring cyclic tetrapeptide JM‐47 and some of its structural variants from a common macrocyclic scaffold has been developed. The key reactions involved a difficult macrocyclization to access the scaffold, and its late‐stage diversification by cross‐metathesis to access the natural product as well as analogues. The synthesis proceeded in good overall yield
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Fusion of Cyclohepta[def]fluorene Units: Toward Synthesis of High‐Spin Non‐Benzenoid Nanographenes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-30 Fupeng Wu, Yubin Fu, Wenhui Niu, Fupin Liu, Renxiang Liu, Zhenlin Qiu, Alexey A. Popov, Junzhi Liu, Ji Ma, Xinliang Feng
Non‐benzenoid diradicaloids possessing high‐spin ground states are attractive synthetic targets given their high potential for spintronics and quantum computing. Nevertheless, the synthesis of such compounds remains highly challenging due to their inherent instability. In this work, we present the synthetic attempt towards creating a non‐benzenoid diradicaloid (1) with a triplet ground state by fusing
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Effect of Tether Length on endo/exo Stereoselectivity in Alkene–Arene meta‐Photocycloaddition Reactions towards the Aphidocolin/Stemodin Scaffolds Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Aljazy A. A. Alshammari, Joseph W. Boyd, Nicola Greaves, Jason G. Kettle, John E. McKendrick, Lewis G. Parker, Andrew T. Russell, Abubakar Sani, Christopher D. Smith
Intramolecular alkene‐arene meta‐photocycloadditions are powerful transformations that use the enhanced reactivity of photoexcited benzene rings to facilitate addition of an alkene 1,3 across donor groups and form complex three‐dimensional fused‐ring systems from readily accessible starting materials. Intramolecular examples have traditionally been restricted to 3‐membered tethers, with cycloaddition
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Direct Palladium‐Catalyzed C5‐Arylation of 1,3,4‐Oxadiazoles with Aryl Chlorides Promoted by Bis(diisopropylphosphino)ferrocene Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Loris Gelin, Henri Sabbadin, Hélène Cattey, Paul Fleurat-Lessard, Jean-Cyrille Hierso, Julien Roger
The direct palladium‐catalyzed C–H arylation of 1,3,4‐oxadiazoles with challenging aryl chloride substrates is promoted by the use of a specifically designed electron‐rich ferrocenyl diphosphane. This protocol employs 0.5 to 1.0 mol% catalyst loading without any additives such as copper or ammonium salts, and equally tolerates electron‐donating and electron‐withdrawing substituents on the (heteroaryl)aryl
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Atropisomeric Properties of 5N‐Benzoyl‐1,5‐benzodiazepin‐2‐ones: Substituent Effects on Rotation around the Ar–N(CO) Axis Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Kaoru Funaki, Hidetsugu Tabata, Hiromi Inyaku, Mizuki Mori, Tomohiko Tasaka, Hideyo Takahashi, Hideaki Natsugari, Tetsuta Oshitari
5N‐Benzoyl‐1,5‐benzodiazepin‐2‐ones with various substituents were synthesized and their atropisomeric properties were analyzed. For the rotational isomers (E/Z) based on the amide bond [N―C(=O)], the E‐isomers were preferentially formed regardless of the substituents. Atropisomers (aR/aS) due to the Ar―N(CO) (sp2―sp2) axis were isolated using chiral HPLC, and the rotational barrier (ΔG‡) in thermal
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Synthesis and Optical and Theoretical Characterization of Imidazo[5,1‐a]isoquinolines and Imidazo[1,5‐a]quinolines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Carina Rössiger, Thomas Oel, Pascal Schweitzer, Olesia Vasylets, Michael Kirchner, Ajlin Abdullahu, Derck Schlettwein, Richard Göttlich
Imidazo[1,5‐a]quinolines emit intense blue luminescence, suggesting their possible use as emitter molecules in organic light‐emitting diodes. We synthesized several new imidazo[5,1‐a]isoquinolines and found they possessed a characteristic hypsochromic effect and even increased quantum efficiency compared to the homolog imidazo[1,5‐a]quinolines, as measured by UV‐vis‐ and fluorescence spectroscopy in
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Topological Structural Chemistry of Fused Bicycloalkanes Allowing Homeomorphic Conversions Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Wataru Setaka
Fused bicycloalkanes have several structures with different orientation of the substituents, such as out,out‐, in,in, and in,out‐structures. Some bicycloalkanes can undergo homeomorphic conversion between certain structures, for instance an out,out‐structure convert to an in,in‐structure. This homeomorphism can be achieved by one chain passing through the macroring. In this report, topological structural
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Synthesis of Sulfo(xo)nium Diacylmethylides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Duo Fu, Jiaxi Xu
Sulfo(xo)nium diacylmethylides (sulfur ylides) are simple, stable, readily prepared, and versatile synthons. Compared with the sulfo(xo)nium monoacylmethylides, they can be compatible with more rigorous reaction conditions and showcase unique characteristics due to their excellent stability. This concept article provides an account for the syntheses of sulfo(xo)nium diacylmethylides, including the
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Synthesis of 2,3‐Diarylindanones and 2‐Arylindenes from Trisubstituted α,β‐Unsaturated Esters Derived from Highly Strained 2,3‐Diarylcyclopropenones and Coumarin Derivatives Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-29 Tanmoy Sahoo, G Siva Sankaram, Myadari Madhu, B Sridhar, B V Subba Reddy
A novel strategy has been developed for the synthesis of 2,3‐diarylindanones and 2‐arylindenes through the formation of trisubstituted α,β‐unsaturated esters by the ring opening of 2,3‐diarylcyclopropenones in the presence ofa catalytic amount of TPP under mild reaction conditions. Initially, PPh3 activates the diarylcyclopropenone to generate the phosphonium adduct, which simultaneously reacts with
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Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-26 Alexander J Hughes, Steven Townsend
We describe the first total synthesis of tabernanthine and ibogaline. Entry to these iboga alkaloid natural products is enabled by a thermal coupling of indoles and aziridines to furnish the requisite nosyl tryptamine starting materials. This route features a Friedel‐Crafts type alkylation to form the key indole‐isoquinuclidine C‐C bond. Finally, a regio‐ and diastereoselective hydroboration‐oxidation
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DBU‐Catalyzed Glutamation of Phenols, Thiophenols, Secondary Amines and Imides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-26 Xue-Ying Wang, Si-Kai Zhu, Mei-Ling Cheng, Ru Jiang, Sheng-Yong Zhang, Ping-An Wang
1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) catalyzed Michael additions between α,β‐unsaturated esters and benzophenone‐imine of glycine esters in THF at room temperature by using LiBr as an additive for glutamation of phenols, thiophenols, secondary amines and imides have been realized. 3‐Substituted glutamic acid esters were obtained in excellent yields and diastereoselectivities (up to quant. yield
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Nickel‐Catalysed syn‐Selective Arylnickelation and Cyclisation of Ketone/Imine‐Tethered Terminal Alkynes with Arylboronic Acids Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-26 Dáiríne Morgan, Hon Wai Lam, Patrick Guiry
Herein we report the first syn‐arylnickelative cyclisation with ketone‐ and imine‐tethered terminal alkynes (16 examples) in yields of up to 89%. The reaction proceeds via a syn‐aryl nickelation of a terminal alkyne followed by cyclisation of the resulting alkenylnickel species onto the ketone or imine. The enantioselective version of this transformation has also been explored with enantioselectivities
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Multicomponent Tandem Cyclization/Aromatization Reaction: Access to 2‐Substituted Naphthothiazoles and Benzothiazoles Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-26 Upendra Kumar, Ajay Sharma, Trayambek Nath Chaubey, Satyendra Kumar Pandey
A straightforward, metal‐free multicomponent tandem cyclization/aromatization approach for the synthesis of naphthothiazoles and benzothiazoles has been described. This method employs α‐tetralone and cyclohexenones as the starting materials, styrene derivatives as a one‐carbon synthon, ammonium salt as the N source, elemental sulfur as the S source, and an oxidant. This approach offers a broad substrate
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Modular Access to Tetrasubstituted N‐H Pyrroles by Catalytic 1,3‐Dipolar Cycloaddition of Azomethine Ylides and α,β‐Ynones Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-26 Qian Huang, Zi-Han Li, Zhen-Ni Zhao, Bo-Ting Chen, Feng-Kai He, Yi-Yong Huang
The development of efficient synthetic strategies for the preparation of tetrasubstituted N‐H pyrrole derivatives, especially in an environmentally benign fashion, still remains momentous, yet challenging. Herein, we report a Cu(II)‐catalyzed tandem reaction of 1,3‐dipolar cycloaddition of α,β‐ynones and glycine iminoesters, followed by Cu(II)‐promoted oxidative (air) dehydrogenative aromatization
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Palladium‐Catalyzed Allylation of Isocyanoacetates with Vinyl Aziridines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-26 Shuang Yan, Zhe-Jia Yu, Zhi-Kun Guo, Jun Zhang, Mei-Xin Zhao
The first palladium‐catalyzed allylation of isocyanoacetates with vinyl aziridines has been developed. The reaction condition was suitable to a variety of α‐aryl isocyanoacetates as well as N‐substituted vinyl aziridines, affording the corresponding allylation products in moderate to high yields (up to 98%) along with excellent stereoselectivity and regioselectivity. The transformations of the allylation
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Copper-Promoted Oxidative Amidation of Imines: A Facile Route to Amides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-20 Zhonghua Cao, Da Sheng, Zhiyang Zhang, Haitao Ren, Yong Liu, Songhai Wu, Jiaxiang Zhang, Xu Han
Herein, an environmentally friendly and efficient amidation method of imines by Oxone and CuO has been developed. This facile method shows excellent selectivity without affecting other functional groups such as phenyls, halogens, cyans, esters or heterocycles. This method features a broad substrate scope, mild conditions and high yields (≤90%), and the yield in the gram scale experiment also reaches
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Selenosulfones, A Meetup of Chalcogens: A Journey into their Recent Chemistry. Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-25 Luana Bagnoli, Ornelio Rosati, Francesca Marini, Claudio Santi, Luca Sancineto
A mini review focused on the chemistry of selenosulfones reported since 2019 is here presented. Initially, methods aimed to the preparation of such moiety are discussed. Successively 1,2‐, 1,3‐, 1,4‐ and 1,7‐addition reactions to C‐C single and multiple bonds are illustrated. The third chapter deals with C‐H functionalizations while the fourth one shows the reactions with aryl diazonium salts or its
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Visible‐Light‐Mediated Alkylation of N‐Heteroarenes Using 2‐Mercaptothiazolinium Salts as Alkyl Radical Source Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-25 Yuan Tian, Xinxin Fu, Ru-Meng Cheng, Jia Feng, Mei-Hua Shen, Chifan Zhu, Hua-Dong Xu
A visible‐light‐mediated radical heteroarylation of 2‑mercaptothiazolinium salts with N‐heteroarenes is reported, furnishing the corresponding functionalized N‐heteroarenes in good to high yields. Various alkyl bromides were converted conveniently into redox‐active thiazolinium salts and subsequently into alkyl radicals by reaction with an excited‐state photocatalyst. This mild protocol permits efficient
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Catalytic Hydroxyethylation of Phenols with Renewable Ethylene Glycol Diester as an Alternative to Ethylene Oxide Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-25 Yu-Ji Luo, Zhi Li
Polyol esters are abundant bio‐based resources. Integration of polyol esters into the production chain of fine chemicals would reduce carbon emission and improve the sustainability of the chemical industry. An efficient synthetic route towards phenoxyethanols was developed through catalytic hydroxyethylation of phenols with ethylene glycol diacetate as the reagent. This method showed the potential
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N‐Heterocyclic Carbene Catalyzed Stetter–Aldol Domino Cyclization To Synthesize Tetrahydronaphthalene‐Fused Spirooxindoles Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-25 Qiuling Xu, Qinghong Cui, Xiaoshan He, Ruifen Sun, Junliang Wang
A formal [4+2] annulation reaction of phthalaldehyde and 3‐ylideneoxindole via a tandem process of Stetter‐aldol reaction was accomplished by the application N‐heterocyclic carbenes as effective catalysts. Under mild conditions, this unprecedented cascade reaction readily occurs in good yield, enabling straightforward access to assemble functionalized tetrahydronaphthalene‐fused spirooxindoles. For
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FeF3‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-24 Xin-Yin Zhou, Wei-Ming Zhang, Cheng-Wei Lu, Hua-Hua Wang, Xiao-Hong Zhang, Xing-Guo Zhang, Hai-Yong Tu
An iron(III)‐promoted radical fluoroalkylation of o‐alkenylaryl isocyanides has been developed using readily available perfluoroalkyl iodides as fluoroalkyl source. This cyclization reaction features broad substrate scope and provides a simple and efficient approach for regioselective construction of biologically important 2‐fluoroalkylated quinolines in 38‐81% yields.
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Direct Synthesis of Monofluoromethylthioesters from Acyl Chlorides with Elemental Sulfur and Fluoroiodomethane Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-24 Chen-Chen Hu, Yu-Yang Zhang, Zeguo Fang, Feng-Ling Qing
We report an unprecedented Ni‐catalyzed direct monofluoromethylthiolation of acyl chlorides, in situ generated from carboxylic acids, with elemental sulfur (S8) as the S source and fluoroiodomethane (ICH2F) as the CH2F radical source to produce a series of monofluoromethylthioesters in moderate to good yields. This approach features excellent functional group tolerance and broad substrate scope. Additionally
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Diastereoselective Synthesis and Functionalization of tert‐Butylsulfinyl‐2‐(chlorodiphenylmethyl)pyrrolidine Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-24 Davide Carboni, Simone Di Remigio, Arianna Quintavalla, Marco Lombardo
The addition of the carbenoid species (chlorodiphenylmethyl)lithium to chiral N‐(4‐bromobutylidene)‐2‐methylpropane‐2‐sulfinamide affords in high yield (up to 81%) and excellent diastereoselectivity (>99:1) the yet undisclosed tert‐butylsulfinyl‐2‐(chlorodiphenylmethyl)pyrrolidine. Preliminary investigations into SN1 solvolysis reactions of this chloride with different alcohols revealed its potential
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Synthesis of 2‐Trifluoromethyl Pyridines through Multicomponent Kröhnke Reaction Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-23 Biqiong Hong, Yun Teng, Zheng Fang, Wei Wu, Zhiqiang Weng
A multicomponent Kröhnke reaction route toward 2‐trifluoromethyl pyridines from reaction of chalcones with easily available and stable 1‐(3,3,3‐trifluoro‐2‐oxopropyl)pyridin‐1‐ium bromide and ammonium acetate is reported. The reaction is found to be general with a range of substituted chalcones, and the applicability of the methodology in gram scale is demonstrated. Preliminary results suggest that
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Iron Photocatalysis Applied to Oxidative Amidation of Aldehydes with NaCl Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-23 Andrea Dellisanti, Luisa Pisano, Massimo Carraro, Andrea Porcheddu, Lidia Vera Giovanna De Luca, Silvia Gaspa
A synthesis of amides from aldehydes promoted by the photoactive complex of Fe2SO4 with 2‐picolinic acid, NaCl as chlorine source, Na2S2O8 as a benign oxidant is reported. The reaction is mediated by visible‐light and is carried out at room temperature in absence of additives. Fe2SO4 is a readily available earth‐abundant metal (EAMs) salt, not needed to be prepared and is environmentally sustainable
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Iron‐Based Deep Eutectic Solvents: Key Players for Amide and Sulfonamide Synthesis and Alcohol Oxidation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-22 Luciana Cicco, Sara Urselli, Claudia Favia, Filippo Maria Perna, Paola Vitale, Vito Capriati
A sustainable protocol has been devised for the oxidation of activated secondary alcohols to their corresponding carbonyl compounds, as well as their utilization as selective mono‐alkylating reagents for both amide and arylsulfonamide derivatives. These reactions proceed smoothly and in good yields (up to 98%) when conducted in Fe‐based deep eutectic solvents (DESs), which serve dual roles as solvents
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Activation/Cyclization of 2H‐Azirines and 3‐Amino‐2‐fluoropyridines Towards 2‐Aryl‐Pyrido[2,3‐b]pyrazines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-22 Tess Fortier, Audrey Belouin, Frédéric Vuillermet, Joanick Bourret, Guillaume Pelletier
The electrophilic activation of 2H‐azirines with triflic anhydride (Tf2O) for an addition/cyclization reaction producing 2‐aryl‐pyrido[2,3‐b]pyrazines regioselectively is described. This reaction proceeds via nucleophilic addition of 3‐amino‐2‐fluoropyridines onto 1‐trifloyl‐aziridin‐2‐yl triflates and subsequent cyclization via SNAr. Desulfonylation and oxidation provides a single regioisomer of the
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Fluoroalkoxylating Reagents in Organic Synthesis: Recent Advances Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-22 Quande Wang, Mingxi Chen
The fluoroalkoxy groups (ORf) are widely used motifs in pharmaceutical and agrochemical fields due to their unique physicochemical properties including higher lipophilicity and increased metabolic stability. Thus, the high value of ORf‐containing derivatives has stimulated the development of fluoroalkoxylation reactions. In this review, we highlight the recent progress of various trifluoroalkoxylating
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Transition-Metal-Free Carbonyl Reduction and Hydrodefluorination of β-Trifluoromethyl Enones with Hydrosilanes: Synthesis of gem-Difluorovinyl Alcohols Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19 Peng-Yuan Zhang, Ya-Fei Hu, Jia-Hao Chu, Ren-Jun Zheng, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu
A transition-metal-free tandem carbonyl reduction and hydrodefluorination of b-trifluoromethyl enones with hydrosilanes was developed for the synthesis of a variety of valuable gem-difluorovinyl alcohols. The hydrosilane could act as both a reductive agent and a C(sp3)-F bond-breaking promotor under mild reaction conditions. Synthetically useful organofluorides, such as gem-fluorophosphine alkene,
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Pd-catalysed indirect and regioselective phosphonation of azobenzenes: toward the design of water-soluble photoswitches Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19 Ivanna AMARSY, Nicolas Gigant, Izel Erturk, Nicolas Bogliotti, Delphine JOSEPH, Sandrine Delarue-Cochin
An efficient palladium-catalysed ortho C-H acyloxylation of azobenzenes, allowing the introduction of the difunctionalised substituent, diethyl phosphonoacetate, is reported. Thanks to the mild reaction conditions implemented, this regioselective late-stage ortho-functionalisation tolerates a wide range of functional groups and permits the access of diversely substituted azobenzenes in good to excellent
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Expression of Concern: One‐Step Synthesis of Biaryls under Mild Condotions Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19
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Synthesis of Noncoded Amino Acids Bearing a Salicylaldehyde Tag for the Design of Reversible-Covalent Peptides Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-19 Mattia Mason, Beatrice Nava, Laura Belvisi, Luca Pignataro, Alberto Dal Corso
Insertion of electrophilic species on the structure of small molecule ligands or peptides is a well-known strategy to increase their binding affinity for the target protein of interest. Among these reactive units, the salicylaldehyde (SA) tag can form remarkably stable imine bonds with the ε-amino group of lysine, a highly frequent residue in proteins. In this work, we describe the optimized synthesis
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Structure-Activity Relationships of Glucose-based PdII-Bis(NHC) Complexes in a Model Suzuki-Miyaura Reaction Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-18 Hannes Ziems, Mirai Komabayashi, Paul Lehmann, Alexander Villinger, Stefan Jopp
The authors of this work have optimized a novel synthetic route towards glucose-based PdII-bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6-iodo-glucopyranosides, followed by acyl-protection, then quaternization with imidazoles and finally the conversion of these acyl-protected glucosyl imidazolium salts to their respective
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Catalyst-free Chloroamination Cyclization Cascade with Sodium Hypochlorite: from N‑(Pentenyl)sulfonylamides to 2‑(1-Chloromethyl)pyrrolidines Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-18 Jacopo Scarfiello, Marco Rusconi, Alberto Lanfranco, Emanuele Azzi, Stefano Caracciolo, Giovanni Ghigo, Polyssena Renzi, Annamaria Deagostino
A mild and catalyst-free protocol to obtain several 2-chloromethylpyrrolidines by the use of a commercial solution of sodium hypochlorite is here reported, without the need for a light source. The choice of the solvent revealed to be crucial in the success of the reaction. Mechanistic studies, both experimental and computational, confirmed a radical mechanism, where the deprotonation step, followed
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Front Cover: A Green Approach to Nucleophilic Aromatic Substitutions of Nicotinic Esters in Cyrene (Eur. J. Org. Chem. 15/2024) Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-18 Andrea Citarella, Miriam Cavinato, Arianna Amenta, Marco Nardini, Alessandra Silvani, Daniele Passarella, Valerio Fasano
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Enantioselective Synthesis of Sterically Hindered α-Allyl-α-Aryl Lactams via Palladium-Catalysed Decarboxylative Asymmetric Allylic Alkylation Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Declan Galvin, Patrick Guiry
The Pd-catalysed decarboxylative asymmetric allylic alkylation (DAAA) of sterically hindered α-aryl,β-amido allyl ester lactams has been developed. The key step in the synthesis of a range of α-aryl lactam substrates for catalysis was a Pb-mediated α-arylation of a β-amido allyl ester affording 14 novel examples of α-aryl-β-amido allyl ester lactams in good yields (up to 80 %). The Pd-catalysed DAAA
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Three-Component Reactions of Alkenes with C–C Bond Formation: Recent Developments Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Zhanyong Wang, Jiarong Li, Tingan Li, Xiaoying Jiang, Hang Li, Ziyan Zhang, Shaohong Xu
Alkenes are highly valuable materials in organic synthesis, and their three-component reactions offer a promising method for C-C bond formation and carbon chain elongation. This approach not only reduces the number of reaction steps but also minimizes waste generation, enabling the preparation of polysubstituted alkanes from simple starting materials. In this review, we provide an overview of recent
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Synthesis and Application of Well-Defined Fluoroalkyl Zinc Complexes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Cai Zhang
Fluoroalkyl groups play an irreplaceable role in the field of pharmaceutical and agrochemical industry due to their unique properties. Based on this, it is crucial to effectively introduce fluoroalkyl groups into target molecules. In this review, we describe the synthesis of well-defined fluoroalkyl zinc complexes and their applications in the fluoroalkylation of compounds. Different from the reactivities
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Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)-Catalyzed sp3 C-H Functionalization Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-17 Shefali Banga, Srinivasarao Arulananda Babu
This paper reports the construction of racemic and enantiopure (D- and L-) fluorene and fluorenone-based novel unnatural amino acid derivatives. The Pd(II)-catalyzed bidentate directing group-aided arylation of prochiral β-C(sp3)-H bonds in racemic, enantiopure carboxamides of amino acids with iodofluorenes was reported. The construction of novel examples of fluorene and fluorenone motifs containing
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Iridium-Catalyzed Electrooxidative Annulation of Naphthol with Acrylate via C-H Bond Activation for the Synthesis of Naphtho[1,8-bc]furan Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Nilam Patil, Debarati Das, Bhalchandra Mahadeo Bhanage
Iridium catalyzed electrochemical coupling of naphthols with acrylates for the syntheses of naphtho[1,8-bc]furan derivatives are herein reported. Ir-catalyzed electrochemical C-H annulation is accomplished within a supportive catalysis manifold, paving the way for electrooxidative C-H acrylation via weak O-coordination. The merge of iridium catalysts and electric current not only minimizes the need
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Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Emeric Montinho-Inacio, Damien Bouchet, Wei-Yang Ma, Pascal Retailleau, Luc Neuville, Géraldine Masson
In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources and employing TBADT as a cost‐effective photocatalyst for direct hydrogen atom transfer (HAT), we achieved successful conversion of these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields and high diastereoselectivity under
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Application of the Photo‐Fries Reaction as a Key Step in the Preparation of Valuable Aryloxyethyl Selenocyanates Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Valentin Lucena, Sergio Hernán Szajnman, Juan Bautista Rodriguez, Sergio Mauricio Bonesi
A multi‐step sequence leads to the preparation of a series of aryl selenocyanate WC‐9 homologues which are interesting compounds with potential biological activity against Trypanosoma cruzi, the etiological agent of Chagas disease. The synthetic sequence involves the application of the photo‐Fries rearrangement reaction as a key step for the preparation of a series of 2‐hydroxyphenones bearing alkyl
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Direct Introduction of an Acetyl Group at the α‐Carbon Atom of an Arene Ring through an Amide Photo‐Fries Rearrangement upon Exposure to UV Light Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Myeonggeuk Kim, Ha-Na Na, Liu-lan Shen, Jin Hyun Jeong
We employed amide photo‐Fries rearrangement for the synthesis benzoheterocyclic compounds and found that a direct acylation of α‐carbon in an arene ring can occur upon exposure to ultraviolet (UV) light. In this reaction, the N‐acetyl group of amides underwent rearranged to the α‐position cross the bridgehead carbon to the other side of the carbon under UV‐C light. The reaction conditions were gentle
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Transfer Hydrogenolysis of O‐ and N‐Benzyl Groups in Water with Tetrahydroxydiboron by Using an Amphiphilic Polymer‐Supported Nano‐Palladium Catalyst Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Kaili Zhang, Shintaro Okumura, Yasuhiro Uozumi
Debenzylation of O‐ and N‐benzyl groups was achieved under safe and mild conditions by using B2(OH)4 as an alternative to gaseous hydrogen in the presence of an amphiphilic polystyrene–poly(ethylene glycol) resin‐supported nano‐palladium catalyst (ARP‐Pd) in water. Benzyl groups of a variety of benzylic ethers, esters, carbamates, and amines, including benzyl‐protected carbohydrates and amino acids
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New Avenues for the Synthesis of Oxa‐Cycles Using Lewis/Brønsted Acid mediated Carboxygenation and Carboalkoxylation of Alkynes Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Santosh Kumar Nanda, Laxmi Narayan Nanda, Juhi Pal, Santosh J. Gharpure
The cascade functionalizations of alkynes have provided many elegant methods for the synthesis of useful scaffolds. Amongst these functionalizations, the ones comprising C‐C and C‐O bond formation have been utilized extensively due to the abundant presence of oxygenated motifs in various bio‐active natural as well as unnatural products. Transition‐metal catalysis is a mainstay for these tandem functionalizations
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Novel Ferrocenyl-azole Derivatives: Synthesis, DFT Calculation and Unlocking the Anticancer Potential Eur. J. Org. Chem. (IF 2.8) Pub Date : 2024-04-16 Vijesh Tomar, Parveen Kumar, Deepak Sharma, Tejveer Singh, Meena Nemiwal, Raj Kumar Joshi
Herein, a series of novel ferrocenyl/phenyl/thiophenyl-azoles was disclosed by vinylic amination of ferrocenyl/phenyl/thiophenyl substituted β-chloro cinnamaldehydes and acrylonitriles. A highly economical and robust chalcogen-stabilized iron selenide carbonyl cluster Fe3Se2(CO)9 worked as an efficient catalyst under aerobic conditions. The amination of ferrocenyl/phenyl/thiophenyl substituted β-chloro-vinylic