Article
Chemistry, Applied
Anton A. Gladkov, Vitalij V. Levin, Alexander D. Dilman
Summary: Aromatic compounds undergo substitution reactions with organozinc reagents under photoredox conditions. The reaction occurs under blue light irradiation with in situ generated organozinc reagents (Barbier conditions), which are oxidized by the photocatalyst, followed by radical attack on the aromatic substrate. This method is effective for polyfluorinated arenes, 2-chlorobenzoxazoles, and 2-sulfonyl-substituted benzothiazole.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Zakhar M. Rubanov, Vitalij V. Levin, Alexander D. Dilman
Summary: Zinc chelate complexes can be formed from N-acyl hydrazones using isopropyl zinc iodide. These complexes can react with alkyl and fluorinated radicals in photoredox reactions. Alkyl radicals are generated from organozinc halides using an organic photocatalyst, resulting in the formation of hydrazines through a reductive mode of addition. Fluorinated radicals are produced from perfluorinated alkyl iodides under photoredox conditions, leading to the formation of fluoroalkylated hydrazones via a neutral reaction pathway.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Enol Lopez, Carlo van Melis, Raul Martin, Alessia Petti, Antonio de la Hoz, Angel Diaz-Ortiz, Adrian P. Dobbs, Kevin Lam, Jesus Alcazar
Summary: This two-step methodology involves the generation of aminal derivatives through anodic oxidation of carboxylic acids, followed by rapid alkylation of iminium ions under flow conditions using organozinc reagents in the presence of BF3 center dot OEt2. It successfully assembles secondary, tertiary, and quaternary carbon centers and can enhance C(sp(3))-functionalities within a molecular framework, making it relevant to drug discovery.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Multidisciplinary Sciences
Margarita Rekhtina, Maximilian Krodel, Yi-Hsuan Wu, Agnieszka Kierzkowska, Felix Donat, Paula M. Abdala, Christoph R. Muller
Summary: The structural dynamics of a NaNO3-promoted, MgO-based CO2 sorbent were investigated using in situ time-resolved powder x-ray diffraction. The sorbent initially deactivates due to an increase in MgO crystallite size, reducing the availability of nucleation points for MgCO3 growth. However, after the third cycle, the sorbent shows continuous reactivation, attributed to the in situ formation of Na2Mg(CO3)2 crystallites that act as seeds for MgCO3 nucleation and growth.
Article
Chemistry, Multidisciplinary
Erin M. Hanada, Patrick J. Mcshea, Suzanne A. Blum
Summary: This study utilizes fluorescence lifetime imaging microscopy (FLIM) to reveal a novel mechanistic role of trimethylsilyl chloride (TMSCl) in metal-catalyzed reactions, which aids in solubilizing organozinc intermediates after oxidative addition, providing a previously uncharacterized mechanistic role for the activating agent.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Brigita Mudrakova, Peter Kisszekelyi, Denisa Vargova, Dorota Zakiewicz, Radovan Sebesta
Summary: This paper presents a highly enantio- and diastereoselective tandem transformation method, using Cu-catalyzed conjugate addition of Grignard reagents to heterocyclic Michael acceptors, followed by one-pot trapping of in situ formed enolates with stabilized carbocations or their equivalents. This method allows the installation of structurally attractive substituents on heterocyclic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Kristen M. Baker, Amanda Tallon, Richard P. Loach, Olivia P. Bercher, Matthew A. Perry, Mary P. Watson
Summary: The deaminative reaction of Katritzky alkylpyridinium salts and sulfinimines has been developed to synthesize enantiopure alpha-chiral amines. This method exhibits excellent diastereoselectivity over the alpha-stereocenter along with broad functional group and heterocycle tolerance.
Article
Chemistry, Organic
Sajjad Ahmed, Mohammad Yaqoob Bhat, Feroze Hussain, Qazi Naveed Ahmed
Summary: In this study, the activation of diphenyl phosphite by BF3/BF4(-) resulted in the formation of thionium ions from aldehydes and thiophenols. These reactive species then reacted with in situ generated phenol, leading to the synthesis of diarylmethyl thioethers. It was found that the addition of external phenol in the reaction yielded unsymmetrical gem-diarylmethyl thioethers in good yields.
Article
Chemistry, Applied
Yishuai Fan, Kaixin Yin, Xiaojie Li, Jinzhe Huang, Ruwei Shen
Summary: This paper describes the development of a tandem conjugate addition-cyclization sequence of p-quinone monoacetals with 2-siloxyphenyl Grignard reagents, resulting in the synthesis of phenol-bridged cyclohexanone derivatives. It also reports a tandem conjugate-addition and dimerization reaction of p-quinone monoacetals with Grignard reagents, leading to the diastereoselective synthesis of complex bridged-ring compounds bearing tricyclo[6.2.2.0(2,7)]dodecene skeletons.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Rowan I. L. Meador, Robert E. Anderson, John D. Chisholm
Summary: Tertiary benzylic alcohols can react with oxoammonium salts in a tandem elimination/allylic oxidation reaction to synthesize allylic ethers in one step, which can then be cleaved under reductive conditions to yield allylic alcohols.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Fang Fang, Jie Xia, Siying Quan, Shanping Chen, Guo-Jun Deng
Summary: A simple and practical method for the preparation of substituted pyrimidines from ketones, NH4OAc, and N,N-dimethylformamide dimethyl acetal is described in this study. The NH4I-promoted three-component tandem reaction offers a broad range of substituted pyrimidines in acceptable yields under metal- and solvent-free conditions. This methodology has the advantages of easily accessible starting materials, simple reaction conditions, and high synthetic yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Arne G. A. Geissler, Bernhard Breit
Summary: The selective addition of chloroprene Grignards to aromatic and aliphatic aldimines, enabled by 2,2'-dimorpholinodiethyl ether (DMDEE), yields the corresponding N-Boc protected S-allenylamines in good yields. The obtained S-allenylamines can be easily deprotected under acidic conditions and can undergo various transformations.
Article
Chemistry, Multidisciplinary
Shiwen Liu, Lingling Meng, Xiaojun Zeng, Gerald B. Hammond, Bo Xu
Summary: This study presents an efficient synthesis of acrylonitriles via a mild and transition metal-free protocol with good chemical yields for a wide range of substrates and good functional group tolerance.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Erandi Liyanage Perera, Daesung Lee
Summary: A new approach for the synthesis of 4-pyrones with broader substrate scope and functional group tolerance is described in this study. The reaction involves the 1,4-addition by piperidine, followed by nitrogen-assisted 6-endo-dig cyclization and hydrolysis. It is found that 1,3-diynones with nonenolizable electron-withdrawing ketones and nonpropargylic H provide high yields. The presence of particular R-2 substituents resulted in the isolation of 1,4-or 1,6-adducts, indicating the strong impact of steric and electronic factors on the 6-endo-dig cyclization.
Article
Food Science & Technology
Cuicui Jiang, Mengyang Liu, Xu Yan, Ruiqi Bao, Aoxue Liu, Wenqing Wang, Zuoli Zhang, Huipeng Liang, Chaofan Ji, Sufang Zhang, Xinping Lin
Summary: The study found that the addition of lipase had little impact on the pH and bacterial community structure of Suanzhayu, but promoted the growth of Proteus and the formation of volatile compounds, accelerating the fermentation process.
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)