Article
Chemistry, Multidisciplinary
Zheng Sun, Shuwei Zhang, Qiyuan Ma, Yuemei Li, Han Ding, Yu Yuan, Xiaodong Jia
Summary: A series of furoxan derivatives with N-nitroso groups were efficiently synthesized by TBN-initiated radical sp(3) C-N bond cleavage of 1-nitromethyl-N-aryltetrahydroisoquinolines. This reaction introduces the biologically important furoxan skeleton and N-nitroso group into one molecule, significantly enhancing molecular complexity through a one-step transformation. Mechanistic studies reveal that this reaction is mediated by the in situ generated alpha-carbonyl nitrile oxide, which is formed via TBN-promoted C-N bond cleavage.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Isabella Wagner, David W. H. Rankin, Sarah L. Masters
Summary: The gas-phase molecular structure of iso-propyl(tert-butyl)(trichlorosilyl)phosphine has been determined using gas electron diffraction and computational methods. Five conformers were found on the potential-energy surface and a combined model with the two most abundant conformers was evaluated. Key structural parameters include rP-Si, rSi-Cl-mean, rP-C-mean, angle P-C-H, angle C-C-C (iPr), angle C-C-C (tBu), and angle C-P-C.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Tianci Li, Jiangyu Yang, Xin Yin, Jinhua Shi, Qun Cao, Miaomiao Hu, Xiaowen Xu, Meichao Li, Zhenlu Shen
Summary: A metal-free photocatalytic Ritter-type C-H amination utilizing molecular oxygen as a terminal oxidant has been developed, offering a cost-effective and sustainable method for synthesizing a broad range of secondary amides under mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Denisa Hidasova, Tomas Slanina
Summary: We present a mild OtBu deprotection catalytic protocol using two commercial reagents: magic blue (MB center dot+), also known as tris-4-bromophenylamminium radical cation, and triethylsilane. Magic blue catalytically facilitates the cleavage of the C-O bond in tert-butyl carbamates, carbonates, esters, and ethers, achieving a high isolated yield of up to 95%, while sacrificial triethylsilane accelerates the reaction. This method is suitable for an array of structurally diverse compounds without the need for high temperatures, transition metals, or strong acidic or basic catalysts.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sourav K. Santra, Alex M. Szpilman
Summary: In this study, a visible-light-mediated benzylic C-H oxygenation reaction has been reported, which can take place at ambient temperature and air pressure with higher yield than current industrial conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Jinliang Song, Manli Hua, Xin Huang, Jun Ma, Chao Xie, Buxing Han
Summary: In this study, a robust bio-derived polyoxometalate (POM) hybrid, PhyA-Mo, was synthesized by reacting naturally occurring phytic acid (PhyA) with MoO3. Systematic studies revealed that the multi-phosphate structure of PhyA allowed PhyA-Mo to simultaneously possess a higher concentration of surface-active oxygen species and more negatively charged Mo sites, enabling outstanding catalytic activity for aerobic oxidation of benzylic C(sp3)-H in different substrates without using any additional initiator. Importantly, this work provided a general and useful strategy to improve the catalytic performance of POM-based materials using phosphoric acids containing multi-phosphate groups.
Article
Chemistry, Organic
Alexandru Caciuleanu, Felix Voehringer, Ivana Fleischer
Summary: We present a catalytic system using non-precious precatalyst Cp2TiCl2 and 2-MeTHF as solvent for direct deoxygenation of benzylic alcohols. Mechansitic studies demonstrate that the silane Me(EtO)(2)SiH not only acts as a H-donor but also as a regenerating agent for the active catalytic species. This method exhibits broad tolerance to various functional and protecting groups, allowing for sequential deoxygenation-dehalogenation and deoxygenation-hydrogenation reactions. The procedure shows successful application in the exhaustive reduction of lignin model substrates.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Shanxue Zhang, Yufeng Li, Tao Wang, Ming Li, Lirong Wen, Weisi Guo
Summary: In this study, we report an electrochemical benzylic isothiocyanation method with high chemoselectivity and site-selectivity under oxidant-free conditions. The method is notable for its compatibility with functional groups and its suitability for late-stage functionalization of bioactive molecules.
Article
Chemistry, Organic
Sudip Sau, Prasenjit Mal
Summary: A convenient one-pot synthesis of quinoxaline-2,3-dione has been achieved by C-H hydroxylation of quinoxalin-2(1H)-one using TBN as a promoter of the reaction in DMSO. First, radical-mediated nitration using TBN at C-3 of quinoxalin-2(1H)-one was carried out, followed by hydroxylation with water via ipso-substitution to obtain quinoxaline-2,3-dione.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Neha Patel, Thambiraja Chokkalingam, Soumyajit Das, Subhrakanti Saha, Karthik Jayaraman, Hemant Bhutani
Summary: A sensitive, reliable, and reproducible method utilizing headspace gas chromatography with flame ionization detection was developed to detect and quantify low levels of tert-butyl nitrite (TBN). The method stabilizes TBN in solution by adding imidazole to the sample diluent and utilizes a high-polarity poly(ethylene glycol) stationary phase for resolution and sensitivity. Validation experiments demonstrated excellent analytical performance in specificity, linearity, precision, and recovery of TBN at trace levels.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Jian Wang, Cheng Zhang, Xiao-Qing Ye, Wenting Du, Shenxin Zeng, Jian-Hong Xu, Hong Yin
Summary: The benzylic aerobic oxidation catalyzed by cheap and simple N-hydroxyimide organocatalyst is efficient and practical, with high yields and broad substrate scope. The catalyst can be recycled, and only a small amount of simple iron salt is used as promoter. This methodology also discusses the influence of substituents, gram-scale application, catalyst decay, and the general mechanism.
Article
Chemistry, Multidisciplinary
Yubin Ma, Fan Gao, Wanru Xiao, Na Li, Shujun Li, Bing Yu, Xuenian Chen
Summary: In this work, two transition metal-containing Nb/W mixed-addendum POM dimers were synthesized and characterized. POM[Fe] was proven to be an efficient photocatalyst for benzylic C-H oxidation under visible light and using oxygen as an oxidant. The results provide insights into the mechanism and effectiveness of POM[Fe] in the oxidation reaction.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Applied
Ankit Kumar Mittal, Gaurav Prakash, Pramod Pathak, Bishal Dutta, Nandita Ahalyan, Siddhartha Maiti, Debabrata Maiti
Summary: Here, we present a flow chemistry method for synthesizing tert-butyl nitrite with a high yield of 95% and a short residence time of 1min, corresponding to a space time yield of 13 g/h/mL. In addition, we demonstrate the application of tert-butyl nitrite in metal-free stereoselective nitration of alkenes. The traditional batch process, with a cycle time of 12 to 24 h, is limited for commercial production. Therefore, we developed a continuous-flow nitration process using a fixed bed column reactor, reducing the reaction time from 12 h to 3 min and achieving a faster and more efficient synthesis.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Organic
Yonggao Zheng, Yanwei Zhao, Suyan Tao, Xingxing Li, Xionglve Cheng, Gangzhong Jiang, Xiaobing Wan
Summary: This study has successfully developed the green esterification of carboxylic acids promoted by tert-butyl nitrite, which is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids can be applied to this reaction under near neutral conditions, with good to excellent yields.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuanyun Gu, Zhen Zhang, Yan-En Wang, Ziteng Dai, Yaqi Yuan, Dan Xiong, Jie Li, Patrick J. Walsh, Jianyou Mao
Summary: The chemoselective deprotonative functionalization of benzylic C-H bonds using LiN(SiMe3)(2)/CsF combination has been found to exhibit excellent benzylic selectivity, leading to the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, even simple substrates like methyl benzoates can react under similar conditions to form the desired products with high selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Shan-Shan Zhu, Yan Liu, Xiao-Lan Chen, Ling-Bo Qu, Bing Yu
Summary: A series of conjugated polymeric photocatalysts based on 4CzIPN were synthesized and optimized photocatalyst CPP3 showed superior visible-light-driven functionalization of C(sp(3))-H bonds with high yields; the enhanced intersystem crossing in CPP3 led to its better photocatalytic performance compared to the monomer 4CzIPN, allowing for easy recovery and reuse.
Article
Chemistry, Organic
Chun-Hua Ma, Lu Zhao, Xing He, Yu-Qin Jiang, Bing Yu
Summary: A novel visible-light-driven catalytic reaction has been developed for the 3-ethoxycarbonylmethylation of 2-aryl-2H-indazoles and imidazo[1,2-a]pyridines using commercially available alpha-bromoesters in water. This protocol offers sustainability, ease of operation, mild reaction conditions, and a wide range of applicable substrates, including alpha-bromoamides for 3-carbamylmethylation products. It has potential applications in drug synthesis like zolpidem and late-stage modification of natural products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Anzai Shi, Panjie Xiang, Yanxuan Wu, Chang Ge, Yan Liu, Kai Sun, Bing Yu
Summary: An efficient method for the synthesis of various arylated 2-aryl-2H-indazoles using an inexpensive photocatalyst 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene has been developed. This protocol shows wide substrate scope, good functional group tolerance, and operational simplicity. Moreover, it has also been successfully applied for the late-stage modification of drug molecules, leading to the introduction of complex drugs into the 2H-indazole skeleton for the first time.
Article
Chemistry, Multidisciplinary
Ru-Nan Wang, Fan -Lin Zeng, Xiao-Lan Chen, Hu-Lin Zhu, Ling-Bo Qu, Xian-Qiang Huang, Shi Tang, Yu-Fen Zhao, Bing Yu
Summary: A series of zinc indium sulfide (ZnIn2S4) photocatalysts were successfully synthesized, with the catalyst ZIS-1 prepared in ethanol showing the highest photocurrent density. Using ZIS-1 as a photocatalyst, the direct C-H azolation of N-heterocycles was achieved under blue light, and the catalyst exhibited good stability and reusability.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Hongfeng Zhuang, Qin Hou, Feng Han, Haotian Lv, Chengxia Miao
Summary: This study established a simple catalytic system for the O-alkylation of oximes with alcohols using H3PW12O40 as the catalyst and dimethyl carbonate as the solvent. The system simplified the reaction systems, realized catalytic transformation, and improved the yields and selectivities.
Article
Chemistry, Physical
Wen -Chao Yang, Yu Sun, Liu -Yu Shen, Xiaoyu Xie, Bing Yu
Summary: In this study, a direct and efficient visible-light-induced cascade cyclization reaction of aryl ynones with 4-alkyl-DHPs was investigated to achieve the divergent synthesis of indenones, thioflavones, and spiro[5.5]trienones via a 5-exo-trig or 6-exo-trig radical cyclization. This cascade reaction demonstrates operational simplicity, metal- and oxidant-free conditions, and excellent functional group tolerance.
MOLECULAR CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yan Liu, Lin Zuo, Qiyan Lv, Bing Yu
Summary: With the rapid growth of photoinduced electron transfer (PET), water-involved photooxygenation reactions based on unsaturated bonds have become diverse and dominant. This mini-review summarizes the recent advances in photochemical transformations using water as an oxygen source since 2020, highlighting the sustainable feature of harnessing water's green properties in photoreactions. Relevant reports are organized comprehensively based on the type of O-containing product targets, including silanols, alcohols, carbonyls, phenols, diaryl ethers, and oxazolines. This review hopes to provide a prospective overview of this topic and stimulate significant research interest.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yan Liu, Xiaolan Chen, Bing Yu
Summary: White phosphorous is a crucial raw material for the phosphorus chemical industry, but its manufacturing processes have negative environmental impacts. This article provides an overview of the recent advances in the photochemical and electrochemical synthesis of P-1 organo-compounds from P-4, with a focus on sustainability. The key aspects of innovation regarding activation mode and mechanism are comprehensively analyzed, and a preliminary outlook on future development is provided.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yong-Hao Li, An-Xiang Huang, Fu-Yi Zhang, Kai Sun, Bing Yu
Summary: A visible-light-induced trifluoromethylalkynylation of 1,6-dialkenes was developed without transition-metal and photocatalyst, allowing the formation of three C-C bonds in a single step. By using a small amount of benzoyl peroxide (BPO) as an initiator, this method enables the activation of alkynyl triflones in a photocatalyst-free manner for the first time to initiate a photocatalytic radical cascade cyclization reaction, showing advantages of high step economy, mild reaction conditions, and broad substrate scope.
Article
Chemistry, Applied
Fan -Lin Zeng, Hu-Lin Zhu, Ru-Nan Wang, Xiao-Ya Yuan, Kai Sun, Ling -Bo Qu, Xiao-Lan Chen, Bing Yu
Summary: Bismuth vanadate (BiVO4-180) synthesized by hydrothermal method at 180 degrees C is a versatile and stable heterogeneous photocatalyst that can functionalize various C(sp2)-H bonds under ambient visible-light conditions. It yields a series of functionalized compounds, including fused heterocycles, tetrahydroquinolines, indoles, amino acid esters, and (hetero)aromatics, in good yields (79 examples, including modified drugs and dipeptide esters). BiVO4 photocatalysts are advantageous due to their recyclability, low cost, air tolerance, and high efficiency, overcoming the limitations of homogeneous photocatalysts.
CHINESE JOURNAL OF CATALYSIS
(2023)
Review
Chemistry, Organic
Ya Liu, Rui Li, Bing Yu
Summary: This minireview summarizes the recent progress in radical-involved transformations of tosyl cyanide via photo-induced reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Hao-Cong Li, Guan-Nan Li, Hao-Sen Wang, Yan Tan, Xiao-Lan Chen, Bing Yu
Summary: A visible-light-induced one-pot three-component reaction was developed for the difunctionalization of alkenes. It showed excellent regioselectivity, broad substrate scope, and high synthetic yield, leading to the synthesis of versatile sulfoximido-cyanoalkylative products.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Fukun Cheng, Lulu Fan, Qiyan Lv, Xiaolan Chen, Bing Yu
Summary: Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents in the visible-light-induced 4CzIPN-catalyzed direct C-H alkylation of N-heteroaromatics. By utilizing this metal-/base-/additive-free photocatalytic system, various alkylated N-heteroaromatic scaffolds were successfully synthesized.
Article
Chemistry, Multidisciplinary
Yan Liu, Lin Zuo, Tianyi Shang, Zhenling Wang, Bing Yu
Summary: Polyfluoroaryl compounds have distinct properties and are widely used in pharmaceuticals, agrochemicals, and materials. Photocatalytic polyfluoroarylation using polyfluoroarenes as radical precursors has become a hot topic in chemical research. This review presents the state-of-the-art in photocatalytic polyfluoroarylation since 2014, covering the basic concept, reaction design, mechanistic insight, and research prospects.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Shan-Shan Zhu, Lin Zuo, Yan Liu, Bing Yu
Summary: A series of hyper-crosslinked porous organic polymers (POPs) were successfully constructed via a facile reaction, and these polymers exhibited excellent photocatalytic performance for aqueous organic transformations under visible light. Furthermore, the POP catalysts showed good stability and reusability properties. These findings contribute to the development of economical, sustainable, and eco-friendly photocatalysts.
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
