Article
Chemistry, Multidisciplinary
Filip G. Zivkovic, Christian D. T- Nielsen, Franziska Schoenebeck
Summary: The departure into unknown chemical space is crucial for the discovery of new properties and functions. In this study, we report the first synthetic access to N-trifluoromethylated formamides, which involves the reduction of stable NCF3 carbamoyl fluorides. The method is characterized by its simplicity and mild reaction conditions, tolerating a wide range of functional groups and stereocenters. Moreover, the newly synthesized N-CF3 formamide motif has been demonstrated to be highly robust and compatible with various chemical transformations, indicating its potential as a building block in complex functional molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Grant J. Dixon, Michael R. Rodriguez, Tyler G. Chong, Kevin Y. Kim, C. Wade Downey
Summary: In the presence of TMSOTf and 2,6-lutidine, a,a-disubstituted aldehydes react with electron rich aromatic aldehydes to form fi,fi-disubstituted styrenes. More electron-rich aromatic aldehydes show faster reaction rates and higher yields. Preliminary results suggest the reaction may proceed via the ionization and formal deformylation of an aldol intermediate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jiang Shao, Nannan Meng, Yuting Wang, Baoshun Zhang, Kaiwen Yang, Cuibo Liu, Yifu Yu, Bin Zhang
Summary: A one-pot electrooxidation method for the synthesis of formamide using a commercial boron-doped diamond catalyst is reported. The method achieves high formamide selectivity and efficiency, and shows potential for large-scale electrosynthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Gorka Calvo-Martin, Daniel Plano, Ignacio Encio, Carmen Sanmartin
Summary: A series of 30 novel N,N-disubstituted selenoureas were synthesized and tested for their antioxidant and cytotoxic activities. Some compounds showed potential anti-cancer properties, with selenourea 6c demonstrating promising anticancer activity in the NCI60 cell line panel.
Article
Chemistry, Inorganic & Nuclear
Jairus L. Lamola, Joy C. Shilubana, Lonwabo Ngodwana, Banele Vatsha, Adedapo S. Adeyinka, Munaka C. Maumela, Cedric W. Holzapfel, Edwin M. Mmutlane
Summary: Researchers have developed two new Pd(II) complexes, suitable for Suzuki-Miyaura cross-coupling reactions. These active catalysts, formed by aminophosphines, show good performance in coupling reactions of aryl bromides and chlorides.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jarvis Hill, David Crich
Summary: A method for the synthesis of hydroxyl-amines under mild conditions with a broad functional group tolerance was developed in this study. Different steric hindrances of magnesium amides require different ligands for optimal reactivity, and a reaction mechanism was proposed to explain the observed reactivity.
Article
Chemistry, Multidisciplinary
Simon Budzak, Justina Jovaisaite, Chung-Yang Huang, Paulius Baronas, Kamile Tulaite, Saulius Jursenas, Denis Jacquemin, Stefan Hecht
Summary: N,N'-disubstituted indigos are photoswitchable molecules that can be controlled by red-light. By tuning the N-substituents, the thermal stability of the molecules can be independently adjusted, while maintaining advantageous red-shifted absorption spectra. Photophysical and computational studies in solvents of different polarities revealed the photoisomerization mechanism of the molecules and the influence of the N-substituents on their switching properties. These mechanistic insights provide guidance for designing molecules with broader applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xiaoling Wang, Jing Li, Yujiro Hayashi
Summary: Peptides and proteins receive significant attention in academia and industry, and the introduction of unusual amino acids allows for the modification of their properties. However, research on peptides with sterically hindered peptide bonds is limited due to the lack of an efficient synthetic approach.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yunxia Feng, Shen Zhao, Guopeng Du, Shuang Zhang, Daopeng Zhang, Hui Liu, Xinjin Li, Yunhui Dong, Feng-Gang Sun
Summary: A novel synthetic method for preparing compounds with all-carbon quaternary stereocenters has been developed in this study. Preliminary mechanistic investigations suggest the involvement of a Ni(i)/Ni(iii) process in the reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Dennis Milesevic, Divya Popat, Patrick Robertson, Claire Vallance
Summary: This study investigates the photodissociation dynamics of N,N-Dimethylformamide using velocity-map imaging. It reveals that excitation at different wavelengths leads to the cleavage of different bonds and the formation of various products, which are influenced by molecular geometries.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Multidisciplinary
Jessica C. Bieniek, Michele Gruenewald, Johannes Winter, Dieter Schollmeyer, Siegfried R. Waldvogel
Summary: The use of electricity as a traceless oxidant provides a sustainable and novel approach to synthesize N,N'-disubstituted indazolin-3-ones through an intramolecular anodic dehydrogenative N-N coupling reaction. This method offers mild reaction conditions, easy experimental setup, excellent scalability, and high atom economy. Various indazolin-3-one derivatives were synthesized with yields up to 78% using inexpensive and sustainable electrode materials and a low supporting electrolyte concentration. Mechanistic studies suggest a biradical pathway and the cleavage of protecting group can be used to access single 2-aryl substituted indazolin-3-ones.
Article
Materials Science, Multidisciplinary
Stterferson Emanoel da Silva, Leonardo Tadeu Boaes Mendonca, Pedro Luiz Guzzo, Alexandre Ricalde Rodrigues, Cecilia Santos Silva, Leonis Luz Lourenco, Severino Alves Junior, Walter Mendes de Azevedo
Summary: Reduced Titania was obtained through laser ablation, with DMF promoting a change in the optical band gap of commercial TiO2. The reduced Titania showed characteristic signals and higher temperatures when excited with a laser.
Article
Biochemistry & Molecular Biology
Mariafrancesca Hyeraci, Laura Agnarelli, Luca Labella, Fabio Marchetti, Maria Luisa Di Paolo, Simona Samaritani, Lisa Dalla Via
Summary: Resistance to cisplatin limits its usefulness as an anticancer drug. This study describes the synthesis and characterization of two new platinum complexes and demonstrates their potential in overcoming cisplatin resistance in cancer cells. The complexes exhibited poor ability to platinate DNA but showed significant intracellular accumulation. Mechanistic studies revealed their ability to inhibit DNA relaxation and activate the apoptotic pathway. Comparison with related complexes provides insights into the resistance phenotype.
Article
Polymer Science
Chuhao Qiu, Weixiang Sun, Tao Wang, Zhen Tong
Summary: When a copolymer network of chemically crosslinked poly(n-butyl methacrylate-co-methacrylic acid) is immersed into a bath of N,N-dimethylformamide (DMF) and water, the network undergoes phase separation depending on the water fraction in the bath. The properties of the swollen network, such as swelling ratio, light transmittance, thermomechanics, dynamical mechanical spectra, and tensile property, were investigated for different water fractions. The results showed that the polymer-rich phase after phase separation became glassy when the water fraction in the bath was above 0.75. This led to a fundamental change in the thermomechanical behavior of the gel. A dynamical gel-to-glass transition was also observed, and its transition temperature decreased with increasing water fraction.
Article
Chemistry, Physical
Syed Ali Abbas Abedi, Weijie Chi, Davin Tan, Tianruo Shen, Chao Wang, Esther Cai Xia Ang, Choon-Hong Tan, Franklin Anariba, Xiaogang Liu
Summary: Understanding the mechanisms of aggregation-induced emission (AIE) is crucial for designing and applying AIEgens, but many AIE systems still lack a clear mechanistic understanding. This study uses quantum chemical calculations to reveal the AIE mechanism of DAN derivatives, emphasizing the importance of manipulating the formation of the TICT state and managing steric hindrance for AIE characteristics.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Chemistry, Applied
Lin-Sheng Lei, Bo-Wen Wang, Da-Ping Jin, Zhu-Peng Gao, Huan-Liang, Shao-Hua Wang, Xue-Tao Xu, Kun Zhang, Xiao-Yun Zhang
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Tian-Lu Zheng, Ye Zhang, A-Long Gou, Fu Cheng, Si-Zhan Liu, Lan Yu, Ming-Yue Cui, Xue-Tao Xu, Kun Zhang, Shao-Hua Wang
Article
Chemistry, Organic
Si-Zhan Liu, Jing Li, Cao-Gen Xue, Xue-Tao Xu, Lin-Sheng Lei, Chen-Yu Huo, Zhen Wang, Shao-Hua Wang
Summary: A copper-promoted cyanation of aryl iodides has been developed using N,N-dimethyl aminomalononitrile as the cyanide source, with moderate toxicity and good stability. This method exhibits a broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Fu Cheng, Dong-Sen Duan, Ye Zhang, Tian-Lu Zheng, Xiao-Yun Zhang, Shao-Hua Wang, Xue-Tao Xu, Dao-Yong Zhu
Summary: The research team achieved the synthesis of two target products through an 11-step synthetic route, utilizing a recently developed tandem reaction as the key step to construct the crucial spirocyclic intermediate.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Da-Ping Jin, Zhu-Peng Gao, Lin Liu, Shi-Qi Cao, Xue-Tao Xu, Xue-Wei Hou, Tian-Lu Zheng, Li-Ming Jiang, Dao-Yong Zhu, Shao-Hua Wang
Summary: The first total synthesis of (+/-)-furanether A, which demonstrates good antifeedant activity, was achieved in 13 linear steps. The key rigid tetracyclic skeleton containing a 1-methyl-8-oxabicyclo[3.2.1]octane moiety with two vicinal quaternary carbon centers was rapidly constructed in one step through a unique tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization sequence.
Article
Chemistry, Organic
Fu Cheng, Dong-Sen Duan, Li-Ming Jiang, Bao-Sheng Li, Jia-Xuan Wang, Yu-Jia Zhou, He-Yu Jiao, Tao Wu, Dao-Yong Zhu, Shao-Hua Wang
Summary: An efficient copper-catalyzed asymmetric ring-opening reaction has been developed, yielding a variety of axially chiral 2-imidobiaryl compounds with excellent enantioselectivities and better convertibility. The synthesis of known chiral ligands with improved efficiency supports the potential utility of this method and its significance in the development of other catalytic asymmetric reactions.
Article
Chemistry, Multidisciplinary
Tian-Lu Zheng, Si-Zhan Liu, Chen-Yu Huo, Jing Li, Bo-Wen Wang, Da-Ping Jin, Fu Cheng, Xiao-Ming Chen, Xiao-Ming Zhang, Xue-Tao Xu, Shao-Hua Wang
Summary: A novel synthesis strategy was developed for functionalized abietane-type diterpenes and related polycyclic molecules using an Au-catalyzed cascade reaction. The key step involved the use of propargylic ester groups for cyclization, leading to successful total synthesis of several target molecules.
Article
Chemistry, Organic
Jing Li, Li -Ming Jiang, Fu Cheng, Yu-Jia Zhou, Dong-Sen Duan, Dao-Yong Zhu, Kun Zhang, Zhuang Xiong, Shao-Hua Wang
Summary: The first total synthesis of sinopyrine B has been achieved in a concise manner with high overall yield in 10 linear steps. The crucial pyrrolo[2,1-a]isoquinoline skeleton, which is widely found in various natural products and pharmacological molecules, was rapidly constructed through a unique cyclization reaction.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Applied
Da-Ping Jin, Shi-Qi Cao, Fu Cheng, Ze-Sen Xue, Run-Ze Li, Yan-Lin Pu, Dao-Yong Zhu, Wen Bao, Xue-Tao Xu, Shao-Hua Wang
Summary: An Au(I)-catalyzed cascade reaction involving cyclization and semipinacol rearrangement of 1,6-enynes has been developed for the synthesis of spiro[4.5]decanes and 7-azaspiro[4.5]decanes. The use of JohnPhosAuCl/NaBARF catalyst led to the formation of functionalizable spirocyclic products with high diastereoselectivity ranging from 6.7:1 to > 20:1 dr. A plausible reaction mechanism has been proposed based on previous literature and experimental findings.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Chen-Yu Huo, Tian-Lu Zheng, Wei-Hao Dai, Zi-Hao Zhang, Jin-Da Wang, Dao-Yong Zhu, Shao-Hua Wang, Xiao-Ming Zhang, Xue-Tao Xu
Summary: A novel polyene cyclization method utilizing the allene group as the initiator has been successfully developed. This efficient strategy enables the construction of an abietane-type tricyclic skeleton with a functionalizable C2-C3 double bond, exhibiting a wide substrate scope and excellent stereoselectivities. The potential utility of this approach has been demonstrated through the total synthesis of seven abietane-type diterpenoids, including the first synthesis of (+/-)-2,3-dihydroxyferruginol and (+/-)-2,3-dihydroxy-15,16-dinor-ent-pimar-8,11,13-triene.
Article
Biochemistry & Molecular Biology
Peng-Fei Zheng, Zhuang Xiong, Cui-Ying Liao, Xin Zhang, Mei Feng, Xiao-Zheng Wu, Jing Lin, Lin-Sheng Lei, You-Cheng Zhang, Shao-Hua Wang, Xue-Tao Xu
Summary: This paper synthesized a series of new compounds showing potential inhibitory activities against alpha-glucosidase and alpha-amylase. Compounds 5g and 5h exhibited bifunctional inhibitory activity against these enzymes and showed no toxicity against cells.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Xiao-Ming Zhang, Bao-Sheng Li, Shao-Hua Wang, Kun Zhang, Fu-Min Zhang, Yong-Qiang Tu
Summary: Semipinacol rearrangement plays a crucial role in organic synthesis, and the development of novel rearrangement reactions has been a vibrant topic that continues to shape the research field. Recent breakthroughs in new electrophiles, tandem processes, and enantioselective catalytic transformations have further enriched the toolbox in this field.
Article
Chemistry, Organic
Sizhan Liu, Mingyue Cui, Bowen Wang, Chunmei Hu, Yingying Zheng, Jing Li, Xuetao Xu, Zhen Wang, Shaohua Wang
Summary: A triethyl amine-promoted cyclization reaction has been developed for the construction of the 6H-1,3-oxazin-6-one skeleton from cyclopropenone and alpha-halohydroxamate. The reaction demonstrates good yield and functional group tolerance under metal-free and mild conditions, making it suitable for gram-scale preparation.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Xuetao Xu, Jie Chen, Junjie Ke, Kun Zhang, Panpan Wu, Shaohua Wang
Summary: Pyrrole, an important heterocycle, is widely found in various functional molecules and materials. Recent advances in pyrrole synthesis focus on different cyclization modes.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Liang Huan, Gou Along, Gao Zhupeng, Lei Linsheng, Wang Bowen, Yu Lan, Xu Xuetao, Wang Shaohua
ACTA CHIMICA SINICA
(2020)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
