Article
Chemistry, Organic
Jindian Duan, Pui Ying Choy, Kin Boon Gan, Fuk Yee Kwong
Summary: A general protocol for N-difluoromethylation of aniline derivatives using commercially available ethyl bromodifluoroacetate as a difluorocarbene source is developed, which exhibits notable operational simplicity, wide functional group tolerance, and good-to-excellent product yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Pengcheng Huang, Xipeng Jiang, Du Gao, Cheng Wang, Da-Qing Shi, Yingsheng Zhao
Summary: A highly regioselective Friedel-Crafts alkylation of arenes was developed using hexafluoroisopropanol as a promoter. Various arenes, including anilides, anisoles, and phenols, were compatible with the reaction, yielding para-alkylated products in moderate to excellent yields. Mechanistic studies showed that hexafluoroisopropanol acted as a weak Lewis acid to activate haloalkanes and coordinated with arenes through hydrogen bonding, leading to highly para-selective alkylated products.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Linfeng Zhang, Jing Zheng, Wenya Zou, Yongqi Shu, Weiran Yang
Summary: A rapid synthesis of 3-iodopropionic acid was conducted using NiCl2 as catalyst in a microwave reactor. Ethyl 3-iodopropionate was dimerized to diethyl adipate under optimal conditions, which can be hydrolyzed to obtain adipic acid.
Article
Chemistry, Multidisciplinary
Hang Yu, Yu Tian, Shuyue Wang, Xin Ke, Rundong Li, Xiaohui Kang
Summary: This study investigated the oxidation mechanism of SANs by Fe(VI) using DFT, revealing that the primary oxidations of SANs follow the HAT mechanism, with the hydroxyl oxygen being more reactive than the carbonyl oxygen. Formation of SAN radicals is crucial, and substituents have a greater influence on the reaction than the position.
Article
Chemistry, Organic
Alejandro Cervantes-Reyes, Aaron C. Smith, Gary M. Chinigo, David C. Blakemore, Michal Szostak
Summary: This study reports a method for the direct synthesis of nitrogen-containing heteroaromatic biaryls by decarbonylative Pd-catalyzed Suzuki cross-coupling. The practical and modular nature of this method enables the synthesis of diverse heterobiaryl products in excellent yields.
Article
Chemistry, Applied
Hongyu Xia, Ganghu Wang, Dongbo Zhao, Chunyin Zhu
Summary: A visible-light-induced oxidative coupling reaction of arylboronic acids for the synthesis of biaryls has been developed. The reaction utilizes polydentate hydrazones as a bifunctional catalyst and proceeds smoothly at room temperature. It is compatible with a wide range of functional groups. The study of UV-Vis spectrum shows that hydrazone and its complex with CuI exhibit major absorptions upon visible-light, indicating the dual role of hydrazone as both ligand and photocatalyst in this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Shuang Wu, Qiong Liu, Quanfeng Zhang, Ya Zhou, Meiyan Liu, Youlin Zeng
Summary: In this study, a new Cu(II) catalyst was reported for the efficient amination of various substrates including aryl boronic acids and anilines. The catalyst showed good reusability and high yields of N-arylation products.
Article
Chemistry, Organic
Rulin Zhao, Zhenqiu Hong, Bei Wang, James Kempson, Lyndon Cornelius, Jianqing Li, Yi-Xin Li, Arvind Mathur
Summary: A simple and efficient method for the synthesis of N1-substituted-4-nitropyrazole-5-carboxylates has been developed, with excellent regioselectivity and good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Qiongwen Kang, Mengdan Wang, Zongkang Wang, Lu Cheng, Yilin Zhu, Chengyu Wang, Yanzhong Li
Summary: A base-promoted selective C2-N1 ring-expansion reaction of indolones toward substituted quinolines under mild conditions has been developed, achieving the cleavage of one C-N bond and three C-C bonds, and the formation of one C-N and three C-C bonds in one step. This is the first example of a transition-metal free ring-expansion reaction of indolones via the selective insertion of alkynoates into the C2-N1 bond.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Meijun Zou, Tianlin Liu, Michael F. Vansco, Christopher A. Sojdak, Charles R. Markus, Raybel Almeida, Kendrew Au, Leonid Sheps, David L. Osborn, Frank A. F. Winiberg, Carl J. Percival, Craig A. Taatjes, Stephen J. Klippenstein, Marsha I. Lester, Rebecca L. Caravan
Summary: Methyl-ethyl-substituted Criegee intermediate (MECI) is a carbonyl oxide formed in the ozonolysis of asymmetric alkenes. It lacks resonance stabilization and reacts faster with SO2 compared to MVK-oxide + SO2, indicating the significant influence of resonance stabilization on Criegee intermediate reactivity.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Organic
Samantha L. Gargaro, Raphael K. Klake, Joshua D. Sieber
Summary: Here, we describe the development of a Cu-catalyzed enantioselective borylative aminoallylation reaction using a N-substituted alleneto access boryl-substituted 1,2-aminoalcohol synthons for generating chiral heteroatom-rich organic compounds. The reaction provides easy access to various substitution patterns of chiral 1,2-aminoalcohol products with high diastereo- and enantioselectivity from readily available starting materials.
Article
Chemistry, Multidisciplinary
Gang Liu, Sen Liu, Zhen Li, Hengyu Chen, Jiashuai Li, Yalin Zhang, Guodong Shen, Bingchuan Yang, Xiude Hu, Xianqiang Huang
Summary: This paper presents a metal- and external oxidant-free electrochemical strategy for the oxidative coupling methodology of amines, leading to functionalized imines in moderate to satisfactory yields.
Article
Chemistry, Multidisciplinary
Jorge Tovar-Rodriguez, Emiliano Fratini, Piero Baglioni, Carlo Ferrari, Jose Antonio de los Reyes-heredia, Yonatan Ramirez-Hernandez, Ignacio Rene Galindo-Esquivel
Summary: Solvothermal synthesis of mesoporous materials based on amphiphilic molecules as structure-directing agents can be enhanced using non-conventional technologies for stirring and thermal activation. Here, we disclose a green synthesis approach for the preparation of cerium-modified hexagonally ordered silica sieves. Ultrasound micromixing enabled us to obtain well-dispersed Ce in the self-assembled silica network and yielded ordered materials with high cerium content (Ce/Si molar ratio = 0.08). Microwave dielectric heating, applied by an innovative open-end coaxial antenna, was used to reduce the overall hydrothermal synthesis time and to improve the surface area and textural properties. These mesoporous materials were used as a Ni catalyst support (10 wt.% metal loading) for the ethanol steam reforming reaction. The new catalysts featured complete ethanol conversion, high H-2 selectivity (65%) and better stability, compared to the same catalyst prepared with magnetic stirring and conventional heating. The Ce-promoted silica sieves offered a suitable support for the controlled growth of nanocarbon that does not result in catalyst deactivation or poisoning after 6 h on stream.
Article
Chemistry, Multidisciplinary
Matthew J. Evans, Mathew D. Anker, Claire L. McMullin, Martyn P. Coles
Summary: In this study, the reaction between potassium aluminyl and various isocyanide substrates was investigated. Different products were obtained depending on the isocyanide used. Degradation of isocyanide and formation of isomeric compounds were observed with tBu-NC. C-3-homologated product and dearomatisation of one aromatic substituent were observed with Dmp-NC. Both C-2- and C-3-homologation products were obtained with Ad-NC, showing control over the chain growth process.
Article
Chemistry, Multidisciplinary
Rongrong Zhao, Simiaomiao Wen, Hao Fu, Mengna Liu, Qixing Liu, Haifeng Zhou
Summary: A simple and efficient synthesis method for various compounds through intramolecular acceptorless dehydrogenative coupling has been achieved using bis(2-methoxyethyl)ether and molecular oxygen. This method does not require an external initiator, catalyst, or additive. The scope of this method was demonstrated through twenty-nine examples and a gram-scale reaction, and control experiments supported a possible reaction pathway.
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)