Article
Chemistry, Multidisciplinary
Achille Antenucci, Stefano Dughera
Summary: A deep eutectic solvent (DES) based on glycerol and KF was used as a solvent medium for cross-coupling reactions between arenediazonium o-benzenedisulfonimides and organolithium reagents (Muharashi-Feringa coupling). The reactions were conducted in open air and mild conditions, resulting in fairly good yields (15 examples; average yield: 60%). This study represents the first example of Muharashi-Feringa coupling carried out with diazonium salts, and a tentative hypothesis for the reaction mechanism was proposed.
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: Reported in this study is a ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols. The usefulness of the method is demonstrated by successfully synthesizing a variety of aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted by overcoming the selectivity issues commonly observed when other transition metals are used as catalysts for C-O cross-coupling reactions.
Article
Chemistry, Organic
Fanpeng Yang, Yina Hu, Lu Wang, Miaomiao Wu, Xiaowen Yuan, Zhigang Liu, Xiuhuan Li, Zhengshen Wang, Huaiji Zheng
Summary: In this study, a palladium-catalyzed cascade Heck cyclization/3-(2-oxindolyl)methylation on intramolecular amination of o-alkynylanilines was developed for the synthesis of indolylmethyl oxindoles. This protocol demonstrated high efficiency, good functional group tolerance, and scalability from easily accessible starting materials.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Avishek Das, Nitin T. Patil
Summary: A ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction between aryl iodides and aliphatic alcohols is reported. The method is demonstrated to be useful for the synthesis of various aryl alkyl ethers, including complex biomolecules and medicinally relevant motifs. The importance of gold catalysis is highlighted in overcoming selectivity issues observed with other transition metal catalysts in C-O cross -coupling reactions.
Article
Chemistry, Multidisciplinary
Bisma Rasool, Irshad Ahmad Zargar, Nazar Hussain, Debaraj Mukherjee
Summary: A convenient method for synthesizing C1-C2 interlinked disaccharides from easily accessible iodo-glycals and unsubstituted glycals is reported. Ester-protected donors and ether-protected acceptors reacted under Pd-Ag catalysis, leading to C-disaccharides with C-3 vinyl ethers. Ring opening by Lewis acid yielded pi-extended conjugated orthogonally protected chiral ketones. Benzyl deprotection and reduction of double bonds resulted in a fully saturated disaccharide stable towards acid hydrolysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Guifang Chen, Bo Xu
Summary: We have developed a C-O cross-coupling reaction between (hetero)aryliodides and silver carboxylates using a Au-I/Au-III catalytic cycle. This transformation shows exclusive chemoselectivity and is insensitive to moisture and air. It is applicable to both aromatic and aliphatic (including primary, secondary, and tertiary) silver carboxylates, and works well in both intermolecular and intramolecular settings. Importantly, high yields are obtained regardless of the electronic effect and steric hindrance of the substrates.
Article
Chemistry, Multidisciplinary
Xin Fang, Chengning Qi, Xiangqian Cao, Zhi-Gang Ren, David James Young, Hong-Xi Li
Summary: This study presents the Cu-catalyzed etherification reaction of phenols with aryl diazonium salts at room temperature, resulting in the formation of diaryl ethers in moderate to excellent yields. The advantages of this method include mild reaction conditions, easy availability of reactants, simple operation, high tolerance towards other functional groups, and convenient work-up. Furthermore, its application in the synthesis of complex biological molecules has been demonstrated. The reaction proceeds through single-electron transfer, extrusion of nitrogen, oxidative addition, and reductive elimination to yield diaryl ether products.
Article
Chemistry, Multidisciplinary
Xianfeng Li, Juan Zhang, Changyang Liu, Jie Sun, Yangfeng Li, Gong Zhang, Yizhou Li
Summary: This article reports on a palladium-catalyzed cross-coupling technique using DNA-conjugated aryl diazonium intermediates for DNA-encoded chemical library synthesis. The method allows for the synthesis of diverse chemical compounds with broad substrate scope and excellent functional group tolerance under mild conditions. It also enables the construction of DNA-tethered pharmaceutical compounds without compromising their bioactivity. This approach demonstrates its potential for creating medicinally relevant combinatorial libraries and investigating protein-ligand interactions in pharmaceutical research.
Article
Chemistry, Organic
Chenpeng Gao, Christopher A. Wilhelmsen, James P. Morken
Summary: Palladium-catalyzed conjunctive cross-coupling can be achieved using chiral phosphine-oxazoline based ligand structures. This reaction specifically works on Grignard-based boron ate complexes and does not require halide-scavenging additives used in other catalyst systems.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chenpeng Gao, Christopher A. Wilhelmsen, James P. Morken
Summary: Palladium-catalyzed conjunctive cross-coupling can be achieved using chiral phosphine-oxazoline ligand structures. Notably, the reaction can be performed on Grignard-based boron ate complexes without the need for halide scavenging additives required by other catalyst systems.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kun-Long Song, Bin Wu, Wan-Er Gan, Yan Zeng, Yu-Jie Zhang, Jian Cao, Li-Wen Xu
Summary: We report a palladium-catalyzed coupling reaction that produces stereodefined silyl-enynes from alkynes and silicon electrophiles with high yields and highly stereoselective formation of either E- or Z-enynes depending on the choice of ligands.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Sangeth Jenthra, Totan Mondal, Gregor Kemper, Marcus Lantzius-Beninga, Markus Hoelscher, Walter Leitner
Summary: A highly chemo- and regioselective decarboxylative Heck-type coupling of carboxylic acids and terminal olefins was achieved using a catalytic system composed of Pd(OAc)(2) in the presence of phosphine-sulfonamido ligands. The bulky ligand L1 favored the formation of 1,1-disubstituted branched olefins with high selectivity, while the less bulky ligand L2 resulted in the formation of 1,2-disubstituted linear products in high yield. Detailed mechanistic investigation revealed that the aryl substituent at the sulfonamide group of ligand L1 favored 1,2-insertion, while the less bulky ligand L2 favored 2,1-insertion.
Article
Chemistry, Multidisciplinary
Yanfang Zhu, Guiyang Xu, Milad Kazemnejadi
Summary: The study successfully achieved competitive asymmetrical C-C* C-C, C-C* C-O, C-C* C-N, and O-C* C-N cross-coupling reactions through a one-pot strategy using a new ionic liquid as solvent, base, and ligand simultaneously. The reactions were performed with high selectivity under mild conditions, based on differences in competitive kinetics and differences in aryl halides' kinetics.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Applied
Evgeniya S. Shutovskaya, Yulia P. Ustimenko, Alexey V. Tkachev, Julia V. Burykina, Alexander M. Agafontsev, Anastasiya V. Lastovka, Dmitriy N. Polovyanenko, Taisiya S. Sukhikh
Summary: In this study, the Pd-catalyzed cross-coupling reaction between α-pinene derivative - pinacarvone O-methyl oxime and aryl halides was described. Surprisingly, the formation of the C-C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The reaction conditions were carefully optimized and the reaction mechanism was proposed based on structural and computational data analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Floriana Vindigni, Stefano Dughera, Francesco Armigliato, Anna Chiorino
MONATSHEFTE FUR CHEMIE
(2016)
Article
Chemistry, Multidisciplinary
Margherita Barbero, Silvano Cadamuro, Stefano Dughera
Article
Chemistry, Multidisciplinary
Margherita Barbero, Giuseppina Cerrato, Enzo Laurenti, Sebastiano Zanol, Stefano Dughera
Article
Chemistry, Organic
Margherita Barbero, Stefano Dughera
Article
Chemistry, Organic
Margherita Barbero, Stefano Dughera, Sara Alberti, Giovanni Ghigo
Article
Chemistry, Physical
Pierpaolo Morgante, Stefano Dughera, Giovanni Ghigo
JOURNAL OF PHYSICAL CHEMISTRY A
(2019)
Article
Chemistry, Organic
Margherita Barbero, Domenica Marabello, Stefano Dughera, Tiziana Sicari, Achille Antenucci, Giovanni Ghigo
Article
Chemistry, Organic
Achille Antenucci, Margherita Barbero, Stefano Dughera, Giovanni Ghigo
Review
Chemistry, Multidisciplinary
Achille Antenucci, Stefano Dughera, Polyssena Renzi
Summary: This review discusses the synthesis of organic chiral catalysts, presents a classification of catalyst scaffolds based on their E factor, and proposes the global E factor (E-G factor) as a new green chemistry metric.
Article
Chemistry, Physical
Achille Antenucci, Matteo Bonomo, Giovanni Ghigo, Lorenzo Gontrani, Claudia Barolo, Stefano Dughera
Summary: This paper investigates the behaviors of arenediazonium tetrafluoroborates in new halide salts/polyol-based DESs, revealing a relatively fast reduction reaction that depends on the electronic effects of substituents. The study aims at elucidating the involved mechanism through computational analysis and experimental approaches.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Chemistry, Organic
Achille Antenucci, Monica Messina, Massimiliano Bertolone, Marco Bella, Armando Carlone, Riccardo Salvio, Stefano Dughera
Summary: The text discusses the use of Solketal, a chiral acetonide of glycerol, in the design of a novel chiral phosphate sodium salt for catalytic applications. The racemate and enantiomers of the substrate can be prepared economically and commercially, allowing for the synthesis of both enantiomers of the final catalyst with simple procedures in high yield. The application of this novel catalyst in a solventless protocol for cyanohydrin synthesis from aldehydes is also presented to demonstrate its usefulness.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Giovanni Ghigo, Matteo Bonomo, Achille Antenucci, Chiara Reviglio, Stefano Dughera
Summary: Deep eutectic solvent (DES)-like mixtures based on glycerol and different halide organic and inorganic salts have been successfully used as new media for copper-free halodediazoniation of arenediazonium salts. The reactions are conducted without the need for metal-based catalysts, at room temperature, and in a short period of time. Pure target products are obtained without the requirement of chromatographic separation. The solvents have been fully characterized and a computational study has been presented in order to understand the reaction mechanism.
Article
Biochemistry & Molecular Biology
Achille Antenucci, Matteo Bonomo, Simone Ghinato, Marco Blangetti, Stefano Dughera
Summary: This study utilized a chiral glycerol derivative to design a new deep eutectic solvent, demonstrating its effectiveness in synthesis and potential as a green alternative.
Article
Chemistry, Multidisciplinary
Achille Antenucci, Francesco Marra, Stefano Dughera
Summary: A chiral heterogeneous catalyst proved to be efficient in a three-component asymmetric Passerini protocol conducted in a deep eutectic solvent. The reaction conditions were mild and environmentally-friendly, with excellent enantioselectivity. The catalyst was easily recovered and reused without any loss in catalytic activity.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)