Article
Chemistry, Organic
Yan Zheng, Siqi Dong, Kai Xu, Delong Liu, Wanbin Zhang
Summary: An efficient Pd-catalyzed asymmetric allylic substitution cascade reaction has been developed for the synthesis of chiral compounds. The reaction achieved high yields and high enantioselectivity under temperature-controlled conditions, and can be performed on a gram scale. The resulting product is versatile and can undergo various transformations.
Article
Chemistry, Organic
Marie-Samira Abdallah, Nicolas Joly, Sylvain Gaillard, Albert Poater, Jean-Luc Renaud
Summary: We report a visible-light-induced iron-catalyzed alpha-alkylation of ketones using a photocatalytic system based on a single diaminocyclopentadienone iron tricarbonyl complex. Two catalytic intermediates of this complex are able to harvest light, allowing the synthesis of substituted aromatic and aliphatic ketones at room temperature using the borrowing hydrogen strategy in the presence of various substituted primary alcohols as alkylating reagents. Preliminary mechanistic studies reveal the role of light for both the dehydrogenation and reduction step.
Article
Chemistry, Organic
Ratnakar Saha, Surajit Panda, Amareshwar Nanda, Bidraha Bagh
Summary: Nickel(II) complex 1 was used as a sustainable catalyst for the alpha-alkylation of arylacetonitriles with challenging secondary alcohols. The reaction tolerated arylacetonitriles with various functional groups and utilized cyclic and acyclic secondary alcohols to yield a large number of alpha-alkylated products. The mechanism involved base-promoted activation of the precatalyst 1 to form an active catalyst 2, which then activated the O-H and C-H bonds of the secondary alcohol in a dehydrogenative pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Xiangchao Xu, Yawen Tang, Jin Zhang, Beixuan Dong, Feng Li
Summary: A ruthenium complex with a functional ligand was found to be an efficient catalyst for the direct N-alkylation of 2-amino-azoles with alcohols, providing 2-(Nalkylamino)zoles with complete regioselectivity. Mechanistic experiments demonstrated the crucial role of functional groups in the bpy ligand for the catalytic activity. This research would advance the development of metal-ligand bifunctional catalysts for the hydrogen autotransfer process.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Ankur Maji, Shivangi Gupta, Milan Maji, Sabuj Kundu
Summary: In this study, a simple, phosphine-free, and inexpensive catalytic system based on a manganese(II) complex was reported for synthesizing important N-heterocycles from amino alcohols and ketones. Control experiments, kinetic studies, and DFT calculations were conducted to support a plausible reaction mechanism. Potential intermediates in the catalytic cycle were detected using ESI-MS analysis, leading to the proposal of a metal-ligand cooperative mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Nicolas Joly, Leo Bettoni, Sylvain Gaillard, Albert Poater, Jean-Luc Renaud
Summary: In this study, a new synthesis method for mono- or dialkylated acyl hydrazide compounds was developed using a diaminocyclopentadienone ruthenium tricarbonyl complex-catalyzed borrowing hydrogen strategy with various substituted primary and secondary alcohols as alkylating reagents. Experimental results confirmed that alcohols were the hydrogen source, and density functional theory (DFT) calculations revealed the differences between mono- and dialkylation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Akash Jana, Sayandip Chakraborty, Koushik Sarkar, Biplab Maji
Summary: In this study, we report the ruthenium-catalyzed synthesis of fi-alkylated secondary alcohols through the regioselective ring opening of epoxides with primary alcohols. The reaction employs alcohol as the carbon source and terminal reductant, and operates through tandem Markovnikov selective transfer hydrogenation of terminal epoxides and hydrogen transfer-mediated cross-coupling of the resulting alcohol with primary alcohol substrates. A broad scope of substrates, including drug and natural product derivatives, is demonstrated with excellent regioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Akash Jana, Sayandip Chakraborty, Koushik Sarkar, Biplab Maji
Summary: Here, we demonstrate a ruthenium-catalyzed method for synthesizing fi-alkylated secondary alcohols through the selective ring opening of epoxides with primary alcohols. The reaction uses alcohol as both the carbon source and the terminal reductant. Kinetic and labeling experiments reveal that the reaction proceeds through tandem Markovnikov selective transfer hydrogenation of terminal epoxides and hydrogen transfer-mediated cross-coupling of the resulting alcohol with primary alcohol substrates. The reaction shows a broad scope, including 40 examples of drugs/natural product derivatives, and exhibits excellent regioselectivity for various substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Biplab Keshari Pandia, Sandip Pattanaik, Chidambaram Gunanathan
Summary: A catalytic cross-coupling reaction of methyldiphenyl-phosphine oxide with arylmethyl alcohols to produce alkenylphosphine oxides was reported using a manganese pincer catalyst. The reactions proceed through aldehyde intermediacy and C=C bond formation facilitated by the catalyst. The use of abundant base metal catalyst and the formation of water and H-2 as the only byproducts make this catalytic protocol sustainable and environmentally benign.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jia-Le Zheng, Fei Liu, Xue Song, Zhi Zhao, Wei Du, Ying-Chun Chen
Summary: In this study, we found that dienones generated from the Morita-Baylis-Hillman carbonates of 2-cyclopentenone under Pd(0) catalysis could be umpolunged through pi-Lewis base activation to form regioselective eta 2-Pd(0) complexes, which then underwent asymmetric inverse-electron-demand oxa-Diels-Alder reaction with alpha-cyano chalcones. This study successfully constructed a range of fused pyran frameworks with dense substitutions and demonstrated excellent stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
Sebastian Stiniya, Padinjare Veetil Saranya, Gopinathan Anilkumar
Summary: N-containing compounds are crucial in nature and synthetic organic chemistry, with N-alkylation reactions playing a significant role in pharmaceuticals and industrial chemical syntheses. Iron-catalyzed N-alkylation reactions have gained acceptance for being environmentally friendly, abundant, non-toxic, biocompatible, reusable, and inexpensive. Green protocols, mild reaction conditions, wide substrate scope, and eco-friendly features make iron-catalyzed N-alkylation reactions prominent in various research fields.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Arjun Gontala, Hyunho Huh, Sang Kook Woo
Summary: Carbon-carbon bond formation is a valuable method for synthesizing amino alcohols, and this study presents a new approach for the divergent synthesis of beta-amino ethers and beta-amino alcohols. The method is efficient, mild, and can be conducted under metal or metal-free conditions. The use of TMSCH2OPMP as a synthetic equivalent of alpha-hydroxymethyl radical allows for in situ photocatalyzed oxidative PMP group deprotection strategy under air. Preliminary mechanistic investigations suggest the involvement of a photoinduced alpha-alkoxy methyl radical and superoxide.
Article
Chemistry, Organic
Changsheng Zhou, Ming Huang, Yufeng Yao, Chunyu Chen, Xin Yi, Ke-fang Yang, Guo-Qiao Lai, Wenjing Xuan, Pinglu Zhang
Summary: In this study, a HFIP-promoted hydroarylation of alkenes with indoles without the presence of transition metal catalysts or additives was reported. The reaction showed efficient, clean and operationally simple characteristics, with a wide substrate scope and versatile transformations, yielding a variety of multi-aryl alkanes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaoyi Zhu, Ruibo Li, Hequan Yao, Aijun Lin
Summary: The palladium-catalyzed allenamide carbopalladation/allylation reaction with active methine compounds resulted in the formation of indoles and isoquinolinones bearing a quaternary carbon center. This reaction demonstrated good efficiency, a broad substrate scope, and good functional group tolerance by forming two new C-C bonds in one pot.
Article
Chemistry, Organic
Balakumar Emayavaramban, Priyanka Chakraborty, Pardeep Dahiya, Basker Sundararaju
Summary: A mild and environmentally friendly approach for alpha-methylation of ketones using methanol as the C1 source under visible light has been developed. The method is applicable to a wide range of ketones with both aromatic and aliphatic backbones, yielding good to excellent product yields. Tentative mechanism has been proposed based on preliminary mechanistic and kinetic experiments.
Article
Chemistry, Inorganic & Nuclear
Min-Jie Zhang, Yu Ge, Chen Cao, Xin-Ran Xue, Qiu-Yi Li, Qi Liu, Jian-Ping Lang
Summary: A flexible metal-organic framework (MOF), {[Cd(1,4-bdc)(4-bpa)]center dot DMF}n (1), was prepared and used to synthesize and store pure interhalogens. The embedded interhalogen molecules were stabilized by interactions with the inner groups of the porous framework and released for organic reactions. This work provides a new approach for the synthesis of pure interhalogens and demonstrates the potential applications of MOF crystal vessels in reactions.
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Mengyao Feng, Fuyuan Liu, Ningwen Yang, Jiayao Yu, Wei Yang, David James Young, Xiang-Qian Cao, Hong-Xi Li, Zhi-Gang Ren
Summary: A heterobimetallic coordination polymer [Au4(dppmt)4(AgCl)2]n (1) incorporating an in situ generated P-S ligand (dppmtH) was synthesized. The structure of 1 contains a one-dimensional helical Au-Au chain. Coordination polymer 1 exhibited a rapid, selective, reversible, and visible vapor chromic response on exposure to methanol (MeOH) vapor.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Zhi-Kang Wang, Ming-Hao Du, Pierre Braunstein, Jian-Ping Lang
Summary: A cut-to-link strategy is proposed to generate high-nuclearity assemblies of low-dimensional metal sulfides, which can contribute to the development of optical materials and models of enzyme active centers. The approach demonstrates the highest non-linear optical absorption coefficient among discrete cluster-based materials reported so far.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Inorganic & Nuclear
Mengling Zhang, Yu Ge, Zheng Qin, Qilei Jiang, Xianggang Huang, Yan Hou, Yingxin Liu, Xueqin Cao, Jian-Ping Lang, Hongwei Gu
Summary: This study demonstrates reversible single-crystal-to-single-crystal (SCSC) transformations between nanoscale three-dimensional ZIF-67 and two-dimensional Co-LDH. The resulting Co-LDH materials show superior oxygen evolution reaction performance, indicating their potential value in crystal synthesis and resource recycling.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yu-Xuan Hong, Meng-Fan Wang, Yu Ge, Hong Yu, Chun-Yan Ni, Wei-Yi Chen, Pierre Braunstein, Jian-Ping Lang
Summary: The solid-state [2 + 2] photocycloaddition experiment introduced in this study provides senior undergraduate students with a comprehensive understanding of coordination chemistry, organic chemistry, structural chemistry, and supramolecular chemistry. This experiment not only strengthens students' experimental skills, but also broadens their research horizon and promotes rigorous thinking in a laboratory course.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Chemistry, Multidisciplinary
Ze-Ming Xu, Zhuoyi Hu, Yali Huang, Shu-Jin Bao, Zheng Niu, Jian-Ping Lang, Abdullah M. Al-Enizi, Ayman Nafady, Shengqian Ma
Summary: Hydrogenated nitrogen heterocyclic compounds are critical in various industries. Previous studies on the partial hydrogenation of these compounds have focused on costly and toxic precious metal catalysts. This research introduces a novel P/B type MOF-FLP catalyst achieved through a solvent-assisted linker incorporation approach, which significantly enhances catalytic hydrogenation reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Da-Liang Zhu, Jie Li, David James Young, Yanqing Wang, Hong-Xi Li
Summary: This paper presents a mild strategy for aminating aryl halides with anilines using dual photoredox and nickel catalysis. Thioxanthen-9-one, an inexpensive and readily available compound, greatly enhanced this cross-coupling reaction, yielding a diverse range of diarylamines in good yields (41-93%) at room temperature. The reaction could be performed under compact fluorescent lamp light or sunlight and was tolerant of various functional groups. It was successfully applied to the synthesis of natural products and drug molecules, even at a gram-scale. The mechanism involves several steps including oxidative addition, transmetalation, energy transfer, and reductive elimination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Shengnan Hu, Sisi Yan, Yuanyuan Hu, David James Young, Hong-Xi Li, Chengrong Lu, Jing-Hui He, Zhi-Gang Ren
Summary: Reliable and sensitive detection of sub-ppm level, ultra-low humidity is critical for a number of important technologies. We report a heteronuclear Au2Cu2 cluster complex that can undergo reversible transformations and has photoluminescent properties in different environments. The crystals of the complex can detect ultralow humidity of 0.21 ppm (w/w).
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
You-Hui Zhao, Hai-Yan Li, David James Young, Xiangqian Cao, Da-Liang Zhu, Zhi-Gang Ren, Hong-Xi Li
Summary: Earth-abundant copper(I) coordination complexes have been developed as visible-light photocatalysts for the intermolecular atom-transfer radical addition reactions. Four heteroleptic bis-chelate Cu(I) complexes were synthesized and showed broad absorption in the visible spectrum. These complexes facilitated efficient reactions with CBr4, CCl3Br, and CHI3, yielding high product yields up to 91%. The substitution on the phpz ligand had a significant impact on the absorption, emission, redox potential, and photocatalytic activity.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Mengyao Feng, Fuyuan Liu, Ningwen Yang, Jiayao Yu, Wei Yang, David James Young, Xiang-Qian Cao, Hong -Xi Li, Zhi-Gang Ren
Summary: A heterobimetallic coordination polymer [Au-4(dppmt)(4)(AgCl)2(]) n (1) with an in situ generated P-S ligand (dppmtH) was synthesized. The structure of 1 contains a helical Au-Au chain connected by [Au(2()dppmt)(2)] dimers. Upon excitation at 343 nm, 1 exhibited cyan phosphorescent emission at QY = 22.3% and t = 0.78 μs. Coordination polymer 1 exhibited a rapid, selective, reversible, and visible vaporchromic response on exposure to methanol vapor, with its emission shifting to a more intense green at QY = 46.8% and t = 1.24 μs.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhi-Hao Zhang, Jia-Lu Ge, Yan Li, Qing Li, Pin-Pin Ma, Xiao-Yan Tang, Wen-Hua Zhang, David J. Young
Summary: Developing porous materials for efficient capture of I-2 is important for the sequestration and storage of radioactive iodine towards clean nuclear energy. In this study, three structurally identical two-dimensional (2D) metal-organic frameworks (MOFs) were prepared, and one of the MOFs showed the highest adsorption capacity for I-2.
Article
Chemistry, Physical
Weichan Zhong, Dixing Chen, Yuting Wu, Jingxiu Yue, Zhangfeng Shen, Hong Huang, Yangang Wang, Xi Li, Jian-Ping Lang, Qineng Xia, Yongyong Cao
Summary: This study proposes a systematic approach to screen efficient double-atom catalysts (DACs) for urea production, using nitrogen and carbon dioxide as precursors, with the help of density functional theory (DFT). The results show that co-doped graphdiyne with CrB and MnB double atoms emerge as potential electrocatalysts for urea production, displaying low energy barriers and the capability to suppress the formation of unwanted by-products. The study establishes a theoretical framework for the evaluation of DACs in electrocatalytic urea synthesis.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2024)
Article
Biochemistry & Molecular Biology
Shan He, Yixiao Wu, Yang Zhang, Xuan Luo, Christopher T. Gibson d Jingrong Gao, Jingrong Gao, Matt Jellicoe, Hao Wang, David J. Young, Colin L. Raston
Summary: Biodegradable cellulose films derived from kombucha, processed using a vortex fluidic device, show increased mechanical strength due to intense micromixing and high shear stress of the liquid film. The films retain their biodegradability and degrade within 5 days.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
