Article
Chemistry, Organic
Penglei Cui, Sida Li, Xianjin Wang, Ming Li, Chun Wang, Lipeng Wu
Summary: In this study, the catalytic deaminative alkylation of phosphine compounds was achieved using visible-light photoredox catalysis. The use of Eosin Y as the photoredox catalyst and visible light significantly promoted the reaction, leading to the successful synthesis of a series of unsymmetrical tertiary phosphines, including compounds with three different substituents that are otherwise difficult to obtain.
Article
Chemistry, Organic
Wen-Wen Zhang, Shao-Ting Gan, Zhao-Yi Qin, Mei Jin, Shan Liu, Wen-Ming Shu, An-Xin Wu
Summary: A DABCO-promoted bicyclization/rearrangement reaction has been developed for the synthesis of tetrasubstituted furans from 1,4-enediones at room temperature. This transformation involves aza-Michael addition, intramolecular bicyclization, and rearrangement processes. In addition, the 4-ureidofuran-3-carboxylate ester products can further be converted to furo[3,4-d]pyrimidine-2,4-diones through intramolecular substitution cyclization under heating conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jing Zhang, Zhiyong Hu, Lan Qin, Yang Gao, Xiao-Qiang Hu
Summary: A dual phosphine/rhodium catalysis was reported for the direct synthesis of unsymmetrical tetrasubstituted alkenes. This method effectively provided diverse carboxyl acid-based tetrasubstituted alkenes through a synergistic merger of phosphine-mediated hydration and rhodium-catalyzed arylation. The resulting carboxylate groups served as universal tags for the synthesis of unsymmetrical tetraarylethenes, demonstrating its utility in material development and drug discovery.
Article
Chemistry, Organic
Atreyee Halder, Debabrata Maiti, Jhilik Dutta, Suman De Sarkar
Summary: The synthesis of unsymmetrical but-2-yne-1,4-diones is achieved through the oxidative alkyne translocation of readily available homopropargylic alcohols. The developed method involves an unprecedented one-pot sequential electro-oxidative annulation-fragmentation-chemical selenoxide elimination process. Excellent functional group compatibility is observed, and a variety of yne-1,4-diones are successfully synthesized. Mechanistic studies through the isolation of key intermediates elucidate the cascade transformation.
Article
Chemistry, Organic
Akashdeep Sharma, Paru Jamwal, Ramani Gurubrahamam
Summary: This study presents a highly efficient and stereoselective route for the synthesis of 1,4-dicarbonyl 2,3-dihaloalkenes. By using stable unprotected alkynyl hydrazones and commercially available N-halosuccinimides, gamma-oxo-alpha, beta-(Z)-dihaloenoates were successfully obtained with high yields and complete Z-selectivity. The protocol also allows for the synthesis of vicinal dihaloalkenes with two different halogen atoms. In addition, a straightforward one-pot synthesis of dihaloenoates from readily accessible compounds was demonstrated, and potential applications of 4-oxo-2,3-dibromoenoates were explored, including the synthesis of valuable five- and six-membered heterocycles.
Article
Chemistry, Physical
Han Huang, Haiyan Zhang, Qiaoling Wang, Youwen Sun, Lei Su, Wenru Xu, Yi Ma, Sheng Kong, Guozhu Zhang, Rui Guo
Summary: We have developed a copper-catalyzed three-component asymmetric radical 1,4-aryl/alkynylation of 1,3-enynes using inexpensive and readily available diaryliodonium salts as precursors. The reaction relies on the use of IPOPA as chiral ligands to generate aryl radicals. This reaction exhibits good compatibility and provides an efficient method for constructing highly enantioselective tetrasubstituted axially chiral allene compounds.
Article
Chemistry, Applied
Roger Monreal-Corona, Alex Diaz-Jimenez, Anna Roglans, Albert Poater, Anna Pla-Quintana
Summary: Predictive catalysis was used to study the reaction between pyridinium 1,4-zwitterionic thiolates and a copper carbene. Theoretical calculations were performed to assess the suitability of their annulation reaction and predict the performance of different copper salts, diazo species, and pyridinium derivatives. The experimental conditions were optimized based on these calculations, the scope of the reaction was evaluated, and the accuracy of the predictions was assessed. Indolizine scaffolds were synthesized with yields up to 90% in the reactivity of pyridinium 1,4-zwitterionic thiolates with a metal carbene.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Caitlyn P. McNichol, Ethan M. DeCicco, Amanda M. Canfield, Daniel P. Carstairs, Shauna M. Paradine
Summary: We present a ligand-enabled, copper-catalyzed aerobic aminooxygenation reaction for internal alkenes. This transformation proceeds via an amidyl radical pathway, different from the previously established aminocupration pathway, through the synergistic combination of a phenanthroline-based ligand and substrate coordination. The switch in reaction mechanism leads to a broadened scope and accessibility to different substrate classes.
Article
Chemistry, Multidisciplinary
Zhi-Zhou Pan, Jia-Heng Li, Hu Tian, Liang Yin
Summary: A copper(I)-catalyzed asymmetric allylation of ketones with 2-aza-1,4-dienes has been demonstrated, providing a series of functionalized homoallyl tertiary alcohols with high to excellent enantioselectivity. The deprotonation of N-allyl-1,1-diphenylmethanimines is the rate-determining step in the reaction, generating nucleophilic allyl copper(I) species. The utility of this method has been demonstrated by the asymmetric synthesis of (R)-boivinianin A and (R)-gossonorol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Na Shao, Valerie Monnier, Laurence Charles, Jean Rodriguez, Cyril Bressy, Adrien Quintard
Summary: This study reports a multicatalytic strategy for the synthesis of a new type of scaffold containing a tetrasubstituted stereocenter embedded in fluorohydrin motifs. The method involves organocatalyzed fluorination and diastereoselective aldol reaction, resulting in the stereoselective synthesis of fluorinated 1,3-diols.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ya Dong, Ruining Li, Junliang Zhou, Zhankui Sun
Summary: This photocatalytic oxidative radical addition reaction utilizes a desulfurization process to generate electrophilic radicals, which add to alpha-halogenated alkenes and undergo further oxidation to deliver unsymmetrical 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.
Article
Chemistry, Multidisciplinary
Cheng Sheng, Zheng Ling, Junzhe Xiao, Kai Yang, Xie Fang, Shengming Ma, Wanbin Zhang
Summary: In this study, enantio- and diastereoselective α-additions of 1-alkynyl ketimines with dual-copper-catalysis were successfully achieved under mild conditions, leading to the synthesis of chiral tetrasubstituted α-amino allenoates bearing a vicinal all-carbon quaternary stereocenter in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >20:1 dr). The stereodivergent synthesis of the products was realized by the asymmetric α-addition reaction and the Grignard reagent promoted epimerization. Importantly, the reaction could be smoothly scaled up and applied to introduce chiral tetrasubstituted allenyl moieties into bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Li Wu, Junrong Chen, Jianwei Xie, Ping Lu, Yanguang Wang
Summary: A facile and efficient copper(I)-catalyzed protocol for the synthesis of 4-boraneyl-1,4-dihydroisoquinolin-3-ones via B-H insertion of copper carbenes has been reported. The reactions exhibit a good scope for the substrate, mild reaction conditions, and high yields, with the products isolated as bench-stable Lewis adducts with Me3N.
Article
Chemistry, Multidisciplinary
Bo-Bo Gou, Yue Tang, Yan-Hong Lin, Le Yu, Qing-Song Jian, Huai-Ri Sun, Jie Chen, Ling Zhou
Summary: A new type of chiral all-carbon tetrasubstituted VQMs was successfully prepared via nucleophilic addition of 2-alkynylnaphthols to o-quinone methides or imines, catalyzed by chiral phosphoric acids. The method showed high efficiency and excellent diastereoselectivities and enantioselectivities, leading to the synthesis of naphthyl-2H-chromenes with axially and centrally chiral elements and axially chiral quinone-naphthols. The obtained axially chiral naphthols could further be converted into valuable phosphine ligands and other functional molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Yantao Li, Qianzhen Shao, Hengchi He, Chengjian Zhu, Xiao-Song Xue, Jin Xie
Summary: The authors present a method to synthesize tetrasubstituted olefins via dual photo- and nickel catalysis under an air atmosphere, without the need for an inert atmosphere. The synthesis of these compounds under mild conditions is challenging, but the authors were able to achieve it by using readily available carboxylic acids and alkenyl triflates. The method shows promise for applications in complex molecule modification and gram-scale synthesis.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Shang-Bo Yu, Furong Lin, Jia Tian, Junlai Yu, Dan-Wei Zhang, Zhan-Ting Li
Summary: WS-POPs have gained attention as water-soluble or dispersible porous organic polymers with well-defined porosity and unique water-processable features. They have shown potential for various applications such as drug delivery, bioimaging, photocatalysis, and membrane separation. Future research is focused on developing new structures and biofunctions for WS-POPs.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Furong Lin, Shang-Bo Yu, Yue-Yang Liu, Chuan-Zhi Liu, Shuai Lu, Jin Cao, Qiao-Yan Qi, Wei Zhou, Xiaopeng Li, Yi Liu, Jia Tian, Zhan-Ting Li
Summary: This study reports the use of porous polymers for neutralizing heparin anticoagulants. These porous polymers show strong binding affinities towards heparins and demonstrate good neutralization effects. The results suggest that porous polymers can serve as effective heparin reversal agents.
ADVANCED MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Shang-Bo Yu, Furong Lin, Jia Tian, Yi Liu, Dan-Wei Zhang, Zhan-Ting Li
Summary: This article introduces the concept and methods of accurate synthesis of two-dimensional polymers with defined layers, and discusses the progress and potential applications in this research area.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Materials Science, Multidisciplinary
Maolin Yu, Weili Zhao, Fan Ni, Qiang Zhao, Chuluo Yang
Summary: This study presents a two-component photoswitchable TADF polymeric nanoparticle (PDFPNs) that incorporates a TADF molecule and a photochromic spiropyran derivative. The PDFPNs exhibit dual-color fluorescence and variable fluorescence lifetime, addressing the issue of TADF quenching by oxygen. The PDFPNs show high FRET efficiency, rapid photoresponsiveness, and excellent photoreversibility, making them promising for bioimaging.
ADVANCED OPTICAL MATERIALS
(2022)
Article
Multidisciplinary Sciences
Zhenghui Luo, Ruijie Ma, Jianwei Yu, Heng Liu, Tao Liu, Fan Ni, Jiahao Hu, Yang Zou, Anping Zeng, Chun-Jen Su, U-Ser Jeng, Xinhui Lu, Feng Gao, Chuluo Yang, He Yan
Summary: Rationally utilizing and developing synthetic units is crucial for designing high-performance non-fullerene small-molecule acceptors. In this study, four acceptors were developed based on a thieno[3,2-b]pyrrole synthetic unit, showing improved photovoltaic properties and energy utilization compared to the standard acceptor IT-4Cl. The ThPy3-based device achieved the highest PCE and excellent FF, while the ThPy4-based device achieved the lowest energy loss and smallest optical band gap.
NATIONAL SCIENCE REVIEW
(2022)
Article
Chemistry, Multidisciplinary
Can Zhang, Chenyin Xu, Cuifen Chen, Junjie Cheng, Hongli Zhang, Fan Ni, Xiaohong Wang, Gang Zou, Longzhen Qiu
Summary: A fundamentally novel approach in designing a programmable circularly polarized light photodetector utilizing the chiral properties of achiral polymers and high-quality film was demonstrated, achieving switchable detection of left- and right-handed CPL signals. This device also exhibited excellent discrimination between different CPL signals, making it a promising tool in various scientific fields and imaging applications.
Article
Chemistry, Multidisciplinary
Zhenghui Luo, Tao Liu, Jiyeon Oh, Ruijie Ma, Jinsheng Miao, Fan Ni, Guangye Zhang, Rui Sun, Cai'e Zhang, Zhanxiang Chen, Yang Zou, Jie Min, Changduk Yang, He Yan, Chuluo Yang
Summary: Moving the central core to the other side is an effective way to achieve isomerization and enhance photovoltaic performance. ThPy6 shows better molecular structure, orientation, and electron mobility compared to ThPy5, leading to excellent performance in organic solar cells.
ADVANCED FUNCTIONAL MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Shuhui Dai, Maliang Tao, Yuan Zhong, Zixiong Li, Jianshu Liang, Dongcheng Chen, Kai Liu, Binbin Wei, Bo Situ, Meng Gao, Ben Zhong Tang
Summary: A series of easily prepared pyrroles that can quickly be transformed into red-to-NIR emissive radical cations in acidic buffer solution and in vivo stomachs have been developed. These in-situ-generated red-to-NIR emissive pyrrole radical cations in the stomach have excellent biocompatibility and stability, and can be used for intravital gastrointestinal imaging with high spatiotemporal resolution, dynamic monitoring of the gastric emptying process, and assessment of anti-gastric-acid therapy.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Xiaosong Cao, Ke Pan, Jingsheng Miao, Xialei Lv, Zhongyan Huang, Fan Ni, Xiaojun Yin, Yaxiong Wei, Chuluo Yang
Summary: In this study, a MR-TADF compound (BN-Se) with efficient spin-flip transition, fast radiative decay, close-to-unity quantum yield, and narrowband emission was reported. The compound showed excellent performance in OLEDs and as a photosensitizer, highlighting its potential beyond OLED applications.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Nanoscience & Nanotechnology
Chao Lu, Youzhen Li, Wenchao Zhu, Yan Yang, Kai Liu, Qingtao Li, Meng Gao
Summary: A self-monitoring theranostic probe TPATCF-S has been developed, which can release H2S quickly under water stimuli and monitor the release by a color change. The TPATCF-S absorbed on alginate dressings can be used for wound exudate-responsive release of H2S to efficiently promote skin wound healing.
ACS APPLIED BIO MATERIALS
(2023)
Article
Materials Science, Multidisciplinary
Yaxun Wu, Fan Ni, Zhanxiang Chen, Wei Yang, Yepeng Xiang, Shaolong Gong, Xiaosong Cao, Chuluo Yang
Summary: In this study, two donor-acceptor-type TADF emitters with highly twisted conformation are synthesized. Through various experiments and analysis, it is discovered that X-aggregation supports aggregation-induced emission behavior, while H-aggregation leads to aggregation-caused quenching.
ADVANCED OPTICAL MATERIALS
(2023)
Article
Nanoscience & Nanotechnology
Wenping Pan, Hongwei Shao, Limin Ma, Xubo Tong, Zicong Zhang, Qian Li, Xin Yang, Kai Liu, Meng Gao, Yingjun Wang
Summary: Organelle-targeted therapy guided by fluorescence imaging holds great potential for precise cancer treatment. However, current therapies can only destroy single organelles, resulting in limited efficacy. To overcome this challenge, researchers have developed a photoactivatable probe that can sequentially destroy multiple organelles in cancer cells, including lysosomes, lipid droplets, and mitochondria. This probe not only eradicates cancer cells efficiently in vitro but also suppresses tumor growth in vivo. Moreover, the probe enables real-time observation of the sequential destruction of multiple organelles through green-to-red fluorescence conversion. This photoactivatable probe provides a new strategy for cancer treatment with greatly improved efficacy.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Organic
Shuang-Gui Lei, You Zhou, Li-Sheng Wang, Zhi-Cheng Yu, Ting Chen, Yan-Dong Wu, Meng Gao, An-Xin Wu
Summary: A novel multicomponent cascade cyclization reaction has been developed for the synthesis of pyrido[3,2-a]phenoxazin-5-ones using simple o-aminophenols, paraformaldehyde, and enaminones. The o-aminophenol serves as a bis-nucleophile and an iminoquinone precursor, facilitating the formation of aminophenoxazinones for the first time through the Povarov reaction, resulting in high-efficiency synthesis of pyrido[3,2-a]phenoxazin-5-ones. These compounds exhibit polarity sensitivity and aggregation-induced emission (AIE) characteristics, making them promising for bioimaging and theranostic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Jian-Da Sun, Yamin Liu, Zijian Zhao, Shang-Bo Yu, Qiao-Yan Qi, Wei Zhou, Hui Wang, Ke Hu, Dan-Wei Zhang, Zhan-Ting Li
Summary: In the past two decades, photodynamic therapy (PDT) has been effective for cancer treatment. However, the residue of photodynamic agents (PDAs) causes long-term skin phototoxicity. This study uses NpBoxes to bind to porphyrin-based PDAs and reduce their content in skin tissues, alleviating posttreatment phototoxicity. The compound 2,6-NpBox can efficiently suppress photosensitivity and reactive oxygen species generation without affecting PDT efficacy.
RSC MEDICINAL CHEMISTRY
(2023)
Article
Materials Science, Biomaterials
Yue Han, Jing Li, Lihua Zheng, Yunhua Chen, Yan Yang, Kai Liu, Yiyue Zhang, Meng Gao
Summary: Bacterial infections with emerging resistance to antibiotics require the development of new antibacterial agents. Researchers have reported a series of antibacterial agents based on positively charged organic groups that can selectively bind and destroy bacterial membranes. To achieve imaging-guided antibacterial therapy, these organic groups often need to be combined with imaging modalities. Researchers have successfully prepared positively charged and deep-red fluorescent supramolecular pyrrole radical cations, which can be used for selective imaging and killing of bacteria.
BIOMATERIALS SCIENCE
(2023)
