Article
Chemistry, Organic
Jiru Shao, Qinyuan Luo, Hongyan Bi, Sunewang R. Wang
Summary: A convenient route to synthesize 3- and 5-ylidenebutenolides from readily available cis-2-acylcyclopropane-1-carboxylates is described. The synergistic activation of vicinal acceptors in cis isomers generates highly strained bicyclic oxocarbenium ion intermediates, while the corresponding trans isomers are inactive under the same conditions due to the difficulty in forming such intermediates.
Article
Chemistry, Organic
Hongchen Li, Lidong Shan, Lin Min, Yunxiang Weng, Xinyan Wang, Yuefei Hu
Summary: A novel tandem synthesis of 1,3-disubstituted naphthalenes is developed using TfOH-promoted directed-aldol and Friedel-Crafts reactions. The discovery of a chemoselective directed-aldol reaction between different ketones with alpha-hydrogens enables the efficient creation of new C-C bonds and a benzene ring in one pot.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Energy & Fuels
Qian Zhang, Youmei Li, Junbo Zhong, Jianzhang Li
Summary: The core issue in photocatalytic H-2 generation is to find high activity, ultra stability, and environment-friendly materials. Graphitic carbon nitride (g-C3N4) is preferred due to its unique qualities and decent stability. However, the low specific surface area and rapid recombination of photo-excited charge pairs limit its industrial-scale production. In this study, CuO/g-C3N4 photocatalysts with different mole ratios were prepared and investigated. The optimal CuO/g-C3N4 catalyst showed significantly improved H-2 evolution rate compared to pure g-C3N4. The formation of CuO/g-C3N4 heterojunctions promoted efficient separation of photo-stimulated charge pairs and enhanced light absorption. This method provides a promising approach for boosting the photocatalytic H-2 generation rate through coupling with transition metal oxides.
Article
Chemistry, Physical
Jun Xu, Ying Luo, Qiaoqi Guo, Hanghang Zhou, Zheng Wang, Hong He
Summary: Platy LaTaON2 with high crystallinity and controlled morphology was successfully synthesized using an innovative preparation method. The platy structure promotes the separation and transfer of photo-generated charge carriers, resulting in improved photocatalytic activity for solar hydrogen production.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Organic
Hui Xu, Hong Chen, Xiao Hu, Guang Xuan, Pinhua Li, Ze Zhang
Summary: An iodine-promoted domino reaction method has been discovered, which allows for the efficient synthesis of a variety of 1,2,4-trisubstituted 5-(o-hydroxybenzoyl)imidazoles. The reaction proceeds in a consecutive manner, involving Michael addition, iodination, cyclization from intramolecular nucleophilic substitution, and dehydrogenative aromatization from spiro ring opening.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Pengfei Han, Tana Tana, Sarina Sarina, Eric R. Waclawik, Chuncheng Chen, Jianfeng Jia, Kun Li, Yanfen Fang, Yingping Huang, William Doherty, Steven E. Bottle, Jincai Zhao, Huai-Yong Zhu
Summary: Plasmonic photocatalysis using silver nanoparticles (AgNPs) has been shown to significantly enhance Lewis acid catalysis for dehydrating sugars to produce 5-hydroxymethylfurfural (HMF) under visible light irradiation. The presence of AgNPs amplifies incident light to high intensities and promotes catalytic activity, leading to a new paradigm in photocatalysis applications.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2021)
Article
Chemistry, Organic
Haidong Liu, Renyi Xing, Kewei Ren, Fei Xue, Chao Feng
Summary: Here, we report a strategically novel method for the efficient construction of indole skeletons using 2-phenylisoxazol-5-ones as starting material. This method involves Bronsted acid-promoted alpha-iminyl cation generation, N-O bond cleavage, and intramolecular cyclization to yield 1H-indole-3-carboxylic acid, which further undergoes decarboxylation. The reaction shows a broad substrate scope and moderate to good yields, making it potentially useful in the pharmaceutical and flavor industries.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Haidong Liu, Renyi Xing, Kewei Ren, Fei Xue, Chao Feng
Summary: Here, we present a novel and efficient method for constructing indole skeletons using 2-phenylisoxazol-5-ones as starting materials. This method proceeds through the generation of alpha-iminyl cations via N-O bond cleavage and subsequent intramolecular cyclization. The desired products, 1H-indole-3-carboxylic acids, can be obtained in high yields within a short reaction time. The broad substrate scope, transition-metal-free reaction condition, and practicality of this method offer great synthetic potential for applications in the pharmaceutical and flavor industries.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chandrahas Tarigopula, Seetharaman Manojveer, Rengarajan Balamurugan
Summary: A novel method is proposed for constructing benzene rings using propargylic alcohols and 1,3-dicarbonyls, involving multiple C-C bond formations to obtain substituted biaryls. The unique reactivity of an acetal formed under the reaction conditions is harnessed in this Bronsted acid-promoted protocol, allowing for the use of alkynyl methyl ketones as a substitute for 1,3-dicarbonyls.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yiming Zhao, Run Yang, Canming Wu, Shihan Wang, Xinghua Liu, Jihui Li, Shuying Xu
Summary: In this study, an unprecedented copper and in situ-generated triflic acid relay-promoted four-component cascade reaction was established for the rapid and concise construction of diverse five-membered cycloguanidines. The reaction involved cyanamides, diaryliodonium triflates, propargylic amines, and water, and resulted in the simultaneous formation of six new bonds with high yields. This reaction provides an alternative strategy for the highly efficient utilization of diaryliodonium triflates by serving as both an arylation reagent and an internal acid promoter.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Xing'an Dong, Kaiwen Wang, Zhihao Cui, Xian Shi, Zhiming Wang, Fan Dong
Summary: In this study, Bi(5)O(7)1 (B01) nanosheets and nanotubes were synthesized to tune the concentration and location of dynamic vacancies through the formation of surface tensile strain. The presence of intrinsic areal defects resulting from surface tensile strain promoted the generation of vacancies at step edge sites. These vacancies facilitated the photocatalytic N-2 activation and reduction. After turning off the light, the surface vacancy sites could be reoccupied by ions, enabling the protection and regeneration of the photocatalyst surface in an aerobic and dark environment. This work provides an innovative strategy for advancing sustainable ammonia production by tuning the concentration and location of surface vacancies on photocatalysts through surface tensile strain.
Article
Engineering, Chemical
Huimin Jin, Yingna Guo, Jie Zhao, Yuyang Bei, Zhengkai Wu, Qingkun Shang
Summary: Bi-Bi5Nb3O15-550 photocatalyst was synthesized by high-temperature calcination and in-situ reduction, with the composition and morphology characterized. The photocatalytic degradation of herbicide 2,4-Dichlorophenoxyacetic acid (2,4-D) under visible light was studied. The introduction of oxygen vacancies and surface plasmon resonance effect of Bi expanded the absorption range and improved the transport of photogenerated carriers, leading to a significant increase in the degradation rate of 2,4-D.
SEPARATION AND PURIFICATION TECHNOLOGY
(2023)
Article
Chemistry, Physical
Qianqian Shen, Baobao Jin, Jinlong Li, Zhe Sun, Wenxiang Kang, Huimin Li, Husheng Jia, Qi Li, Jinbo Xue
Summary: Developing technologies for high-yield photocatalytic hydrogen production reactions faces significant challenges due to low utilization of light, rapid recombination of photogenerated electron-hole pairs, and a limited number of active sites. In this study, researchers designed and fabricated a three-dimensional TiO2 rutile/anatase array photocatalytic material using an in situ dissolution-recrystallisation approach. The unique nanoarray structure and in situ fabrication of the AE-TiO2 homojunction improved light harvesting efficiency, charge transport separation efficiency, and surface active sites, leading to enhanced photocatalytic hydrolysis performance.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2024)
Article
Chemistry, Physical
Jin-Meng Yang, Ke-An Wang, Hai-Bin Zhu
Summary: Rational design of CoO/Co-N-C hybrid electrocatalyst with excellent oxygen reduction reaction (ORR) activity and methanol tolerance has been achieved by high-temperature pyrolysis and chemical treatment. The home-made zinc-air battery using the catalyst as the air-cathode exhibits good performance in terms of open-circuit voltage and power density.
JOURNAL OF ALLOYS AND COMPOUNDS
(2022)
Article
Engineering, Chemical
Yixuan Lv, Dandan Ma, Chao Yang, Kunli Song, Le Shi, Yonghong Cheng, Chunming Niu, Jian-Wen Shi
Summary: A heterojunction composed of CsCu2I3 perovskite and graphite carbon nitride (CN) was constructed for the first time, resulting in significantly enhanced photocatalytic hydrogen evolution performance. The hydrogen evolution rate of the heterojunction was 2212 umol/g/h, four times higher than CsCu2I3 and nearly ten times higher than CN. The formation of a unique N-I bond at the interface between CN and CsCu2I3 facilitated the transfer of photogenerated electrons, establishing a type II mechanism and effectively promoting hydrogen evolution.
SEPARATION AND PURIFICATION TECHNOLOGY
(2023)
Review
Chemistry, Multidisciplinary
Charnsak Thongsornkleeb, Jumreang Tummatorn, Somsak Ruchirawat
Summary: This review summarizes the synthetic strategies and methods currently known in the literature for the construction of four important indoloquinoline skeletons. The bioactivities of these compounds in the field of medicine are also discussed.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Nattawadee Chaisan, Sureeporn Ruengsangtongkul, Charnsak Thongsornkleeb, Jumreang Tummatorn, Somsak Ruchirawat
Summary: This article introduces a convenient method for the synthesis of 2,2-dihaloketones and gem-dihalolactols. It can be applied to a wide range of substrates to obtain the corresponding products with varying yields.
Article
Chemistry, Organic
Sureeporn Ruengsangtongkul, Takahito Kuribara, Nattawadee Chaisan, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: Unsymmetrical 1,1,2-triacylalkenes can be conveniently prepared by using ceric ammonium nitrate as the oxidant. The method is mild, practical, and can be conducted under air.
Article
Chemistry, Organic
Warabhorn Rodphon, Kanokwan Jaithum, Sutida Linkhum, Charnsak Thongsornkleeb, Jumreang Tummatorn, Somsak Ruchirawat
Summary: A cascade oxazole-benzannulation method has been developed for the synthesis of naphtho[2,3-d]oxazoles with a wide variety of substituents. This method offers the advantage of easy accessibility of substrates and the ability to prepare substrates from a variety of commercially available starting materials.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Pavitra Laohapaisan, Onrapak Reamtong, Jumreang Tummatorn, Charnsak Thongsornkleeb, Urusa Thaenkham, Poom Adisakwattana, Somsak Ruchirawat
Summary: We have discovered a lead compound, N-methylbenzo[d]oxazol-2-amine (2a), that is comparable in potency to albendazole, an orally administered anthelmintic drug, against Gnathostoma spinigerum, Caenorhabditis elegans, and Trichinella spiralis. Compound 2a exhibits significantly lower cytotoxicity towards normal human cell line (HEK293) compared to albendazole. Additionally, we have developed a novel metal-free synthesis method for N-alkylbenzo[d]oxazol-2-amine and N-alkylbenzo[d]thiazol-2-amine derivatives, particularly N-methylbenzo[d]oxazol-2-amine and N-methylbenzo[d]thiazol-2-amine derivatives which are difficult to prepare using other metal-free conditions. Furthermore, proteomic analysis of compound 2a was also conducted in this study.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Warabhorn Rodphon, Sutida Linkhum, Charnsak Thongsornkleeb, Jumreang Tummatorn, Somsak Ruchirawat
Summary: The synthesis of aryl(1-indanyl)ketones was achieved by generating reactive carbocation intermediates from ortho-alkynylarylmethanol substrates. Substrates with a tertiary carbon at the beta-position to the arene generated a carbocation intermediate through dehydration/protonation, followed by cyclization and hydration. Substrates with a quaternary carbon at that position generated a carbocation intermediate through protonation/elimination of water, followed by a 1,2-shift and subsequent cyclization/hydration to give highly substituted indanylketones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kunlayanee Punjajom, Sureeporn Ruengsangtongkul, Jumreang Tummatorn, Praneet Paiboonsombat, Somsak Ruchirawat, Charnsak Thongsornkleeb
Summary: A general protocol for oxidative annulation was developed to prepare 2-methyl-3,4-diacylquinolines directly from 2-alkynylanilines and 1,3-ketoesters. The reactions were mediated by Mn(OAc)3 in acetic acid at room temperature, leading to the desired quinoline products in one-pot in low to good overall yields on a wide range of substrates. The current method is convenient, conducted under mild conditions, and has short reaction times.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Jumreang Tummatorn, Somsak Ruchirawat, Charnsak Thongsornkleeb
Summary: Halogenative annulation of alkyne-tethered N- and O-containing arenes is a general strategy for constructing various halogenated N- and O-heterocycles. This method provides valuable synthetic building blocks carrying C(sp2)- halide functional groups, which are useful for cross-coupling reactions and other transformations. This Short Review examines different halogenative annulation methods for constructing aryl-fused halogenated N- and O-heterocycles, with a focus on recent technologies and the roles of halogenating agents.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Nitwaree Palavong, Piyaporn Arunkirirote, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: This work presents a novel approach for synthesizing quinazolino[3,2-a]quinazolinone derivatives through C-H functionalization catalyzed by ligand-free copper. The reaction offers a convenient protocol that can be applied to a wide range of substrates, yielding excellent product yields. Furthermore, this method has the advantages of generating minimal waste, short reaction times, and readily available starting materials.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jantra Jantrapirom, Phornphan Yongpanich, Jumreang Tummatorn, Kittipong Chainok, Suwadee Jiajaroen, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: This work presents a new method for synthesizing cyclopenta[a]naphthalenol and 2-phenylnaphthalen-1-ol analogs through selective cyclization reactions. By using ortho-alkynylarylkenones as the substrates and specific acids, the authors successfully achieved selective cyclization to produce the desired products. The switch of acid type allowed the synthesis of different compounds. Furthermore, the authors demonstrated the utility of 2-phenylnaphthalen-1-ol in preparing other important compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jantra Jantrapirom, Phornphan Yongpanich, Jumreang Tummatorn, Kittipong Chainok, Suwadee Jiajaroen, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: This work presents a novel method for synthesizing cyclopenta[a]naphthalenol and 2-phenylnaphthalen-1-ol analogs using selective cyclization. The common substrates used were ortho-alkynylarylkenones prepared through Sonogashira coupling. The reaction conditions and solvents employed allowed for the selective cyclization to occur, yielding the desired products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Prapas Khorphueng, Jumreang Tummatorn, Wacharakorn Patumanon, Charnsak Thongsornkleeb, Sukit Chonradeenitchakul, Somsak Ruchirawat
Summary: This study developed a synthesis method for 2,4-disubstituted-1-naphthols using photomediated C-C bond cleavage. The results showed that indenone precursors containing aryl substituents could provide the desired products with yields up to 81%.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
