Article
Chemistry, Applied
Yan-Rui Zhao, Lei Li, Jun Xuan
Summary: In this study, a direct synthesis method for indolines through visible-light irradiation at room temperature without the addition of any photocatalysts and additives was reported. Mechanism studies showed the formation of an electron donor-acceptor complex between iodonium ylides and tertiary aryl amines during the reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Kai N. Sands, Benjamin S. Gelfand, Thomas G. Back
Summary: Aryl selenonic acids were synthesized from aryl bromides via a one-pot method, with yields ranging from 77-90%. The synthesis involved metalation, selenation, oxidation with hydrogen peroxide, and ion exchange. One derivative readily dehydrated to form a cyclic selenonic ester, while two minor byproducts were identified as mixed salts of aryl selenonic acids with either aryl seleninic or selenious acid through X-ray crystallography.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Florian Papp, Daniel Sowa Prendes, Sourav Manna, Ann-Katrin Seitz, Sofiya Kostiukovska, Julian Loeffler, Viktoria H. Gessner, Lukas J. Goossen
Summary: Palladium complexes with ylide-functionalized phosphine ligands catalyze the arylation of N-protected hydantoins with aryl chlorides, enabling the synthesis of a wide variety of hydantoins, including derivatives of the anticonvulsant drugs phenytoin and mephenytoin. Selective monoarylations, sequential diarylations, and arylation-alkylation sequences have been achieved, along with stepwise deprotection strategies.
Article
Chemistry, Organic
Shaikh Samser, Priyabrata Biswal, Sushanta Kumar Meher, Krishnan Venkatasubbaiah
Summary: The one-pot synthesis of Robinson annulated 3-aryl-cyclohexenones from allyl alcohols and ketones using palladium catalyst is reported. Long chain aliphatic or aryl substitutions at the C1 position of allyl alcohol lead to the formation of 1,5-diketone products. This method eliminates the need for highly electrophilic vinyl ketones, making the reaction simpler.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiaojing Xu, Huan Luo, Jiayi Shen, Jing Chen, Jie Ye, Ze-Feng Xu, Chuan-Ying Li
Summary: Valuable piperidin-4-one derivatives were synthesized efficiently via an α-imino carbene-initiated cascade reaction, demonstrating excellent alkyl migration selectivity facilitated by 2-bromoethyl neighboring group participation. This protocol is characterized by high efficiency, excellent migrating selectivity, broad substrate scope, and convenient one-pot procedure, making it an effective tool for piperidine derivative synthesis. The migration-annulation reaction of α-imino carbene presents a powerful strategy for heterocycle construction.
Article
Chemistry, Organic
Zhi-Cheng Yu, You Zhou, Xiang-Long Chen, Jin-Tian Ma, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu
Summary: A reductive coupling reaction was established for the synthesis of diaryl 1,2-dicarbonyl compounds from aryl methyl ketones. The reaction involves C(CO)-C(sp3) bond cleavage and proceeds through an electron transfer process. Notably, this reaction is simple to operate, has mild reaction conditions, and is applicable to a wide range of substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Linhao Liu, Henri Doucet
Summary: The reactivity of 1,2-dihalobenzenes in palladium catalyzed polyheteroarylation via C-H bond functionalization was investigated. The first catalytic cycle using thiophene as the heteroarene gives the expected 2-(2-bromophenyl)thiophenes. In the course of the second catalytic cycle, in the presence of heteroarenes having a free C3-position, a partial Pd-1,4-migration occurred giving rise to aryl-substituted biheteroarenes such as 2 '-aryl-2,3 '-bithiophenes as well as the expected 1,2-di(thiophen-2-yl)benzenes. The best selectivities in favor of the formation of 2 '-aryl-2,3 '-bithiophenes were obtained with electron-rich 1,2-dihalobenzenes. A wide variety of thiophene derivatives bearing useful functions such as formyl, acetyl, cyclopropylmethanone, 2-methyl-1,3-dioxolane, ester, nitrile or chloro was tolerated allowing to prepare poly-functionalized 2 '-aryl-2,3 '-bithiophenes. Moreover, this one pot preparation of 2 '-aryl-2,3 '-bithiophenes employs a low loading of an air stable commercially available palladium source associated to an inexpensive base.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Qingru Wen, Shuo Chen, Chaoqun Shi, Shuai Chen, Yanru Ji, Jian Guo, Zhengli Liu, Yun He, Zhang Feng
Summary: In this study, iron-catalyzed decarbonylation of aryl and alkyl carboxylic acids has been developed, providing the corresponding borylated products with good efficiency. This protocol features excellent functional group compatibility and mild conditions, offering new opportunities for applications in medicinal chemistry and organic synthesis.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Organic
Shubhendu S. Karandikar, Bryan E. Metze, Riley A. Roberts, David R. Stuart
Summary: In this study, a one-pot reaction involving diaryliodonium and aryne intermediates is used to substitute the boron group and ortho-hydrogen atom in arylboron compounds. The method demonstrates the versatility of arylboron reagents and arynophiles, and is applied to the formal synthesis of a potential drug candidate.
Article
Chemistry, Organic
Daohong Yu, Yungen Liu, Chi-Ming Che
Summary: A synthetic method for constructing trifluoromethyl-pyrrolo[2,1-a]isoquinolines via decarboxylation and photocatalytic reactions is described. This method exhibits broad substrate compatibility and enables facile access to pharmaceutically active derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Peng Wang, Ji Yang, Kangkang Sun, Helfried Neumann, Matthias Beller
Summary: The direct palladium-catalyzed selective carbonylative coupling of less reactive aryl chlorides with primary and secondary amines is achieved using a palladium/Xantphos catalyst system and cesium chloride as an additive. This reaction shows high conversion for various aryl chlorides and good functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Majdi Hajri, Omar Khoumeri, Raoudha Abderrahim, Thierry Terme, Patrice Vanelle
Summary: A novel series of pyrido[2,3-b]quinoxaline-3-carboxylate derivatives was efficiently synthesized in short reaction times and with moderate to good yields using a palladium catalyst in a one-pot Buchwald amination/cyclization reaction.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Jun Li, Zhi-Wen Zhao, Shuang Zheng, Ping He, Ji-Ying Qiu, Quan-Quan Zhou, Zhi-Lin Ren
Summary: Herein, we describe a novel one-pot method for the synthesis of polysubstituted pyrrole derivatives via a three-component reaction of alkenyl bromides, amines, and isocyanides. The conversion process is catalyzed by a Pd catalyst without the need for additional ligands. The key feature of this method is the orderly insertion of three isocyanide molecules, directed by the intramolecular imine group. Additionally, DFT calculations provide support for the proposed reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Kai-Rui Feng, Yun-Xuan Tan, Wenbo Ye, Yi-Fan Wang, Zhi-Tao He, Ping Tian, Guo-Qiang Lin
Summary: The study successfully achieved Cu-catalyzed asymmetric carboboration of cyclohexadienone-tethered allenes, resulting in cis-bicyclic frameworks with high enantioselectivities. Further conjugate borylation improved the overall enantioselectivity, and one-pot preparation of highly enantioenriched tricyclo[5.2.2.0(4,9)]undecanes was developed.
Article
Chemistry, Multidisciplinary
P. Veeraraghavan Ramachandran, Henry J. Hamann, Sukriti Mishra
Summary: A rapid synthesis of aminoboranes from amine-boranes utilizing an iodination/dehydroiodination sequence is described. It has been applied to a one-pot palladium-catalyzed conversion of iodo- and bromoarenes to the corresponding boronates, and allows for recovery of the utilized amine.
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)