Article
Chemistry, Organic
Xingwang Deng, Guan Zhou, Xiao Han, Khadim Ullah, Rajavel Srinivasan
Summary: Potassium acyltrifluoroborates (KATs) are opening up new avenues in chemical biology, materials science, and synthetic organic chemistry due to their intriguing reactivities. The chemoselective Pd-catalyzed approaches developed for the late-stage diversification of arenes bearing prefunctionalized KATs feature chemoselective cross-coupling, rapid diversification, functional group tolerance, mild reaction conditions, simple operation, and high yields.
Article
Chemistry, Applied
Andrej Sterman, Janez Kosmrlj, Nina Zigart, Stanislav Gobec, Izidor Sosic, Zdenko Casar
Summary: A series of structurally diverse benzyl protected trifluoroborate-ammoniums were efficiently prepared by hydrogenation of corresponding trifluoroborate-iminiums using Crabtree's catalyst, with subsequent deprotections yielding alpha-aminoboronic acids. Initial experiments on asymmetric reactions showed a correlation between E/Z-ratio in the substrate and enantioselectivity, highlighting the potential of this method for accessing libraries of alpha-aminoboronic acid derivatives for medicinal chemistry applications and beyond.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Andrej Sterman, Izidor Sosic, Zdenko Casar
Summary: This work describes the preparation and application of primary trifluoroborate-iminiums (pTIMs) as a new and valuable class of organoboron derivatives. Highly enantioselective hydrogenation reactions were used to obtain chiral primary trifluoroborate-ammoniums (pTAMs). A facile conversion method using hexamethyldisiloxane/aqueous HCl was then used to synthesize diverse chiral alpha-aminoboronic acids from chiral pTAMs. The synthesis of optically pure anti-cancer drugs bortezomib and ixazomib demonstrated the practicality of this method.
Article
Chemistry, Organic
Ying-Ying Peng, Bi-Yin Zhuo, Zhi-Qiang Wang, Bang Liu, Fu-Xing Zhang, Jiang-Xi Yu, Cheng-Yong Wang, Zhi-Feng Xu, Jin-Heng Li
Summary: A room temperature Mg((OBu)-Bu-t)(2)-catalyzed C(sp(3))-H oxidation of alpha-azido arylethanones to produce primary alpha-ketoamides is presented. By utilizing TBHP as the oxidant and carbonyl oxygen source, this method allows the oxidation of dual methylene C-H bonds alpha to the carbonyl group for the synthesis of various primary alpha-ketoamides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ramachandra Reddy Putta, Simin Chun, Seok Beom Lee, Junhwa Hong, Seung Hyun Choi, Dong-Chan Oh, Suckchang Hong
Summary: An iron catalyst system that achieves chemoselectivity between borrowing hydrogen and dehydrogenative coupling protocols by simply changing the base is reported. The system can selectively and efficiently convert a broad range of nitriles and alcohols to the corresponding products, with environmentally benign and atom-efficient characteristics.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Nalladhambi Neerathilingam, Sakthivel Prabhu, Ramasamy Anandhan
Summary: Electrochemical synthesis of phthalimides from o-phthalaldehyde and amines through tandem cyclocondensation and alpha-C-H oxygenation of isoindolinone was achieved. The alpha-C-H oxidation was carried out with molecular oxygen via an oxygen reduction reaction (ORR) on the cathode under electrochemical conditions. The synthetic protocol demonstrated its utility through gram-scale synthesis and obtaining bioactive molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Hu-Lin Zhu, Fan-Lin Zeng, Xiao-Lan Chen, Kai Sun, Hao-Cong Li, Xiao-Ya Yuan, Ling-Bo Qu, Bing Yu
Summary: The study describes a general and metal-free visible-light-induced decarboxylative arylation method at room temperature. This practical method uses 4CzIPN as a photocatalyst under mild conditions, avoiding the need for additional base, traditional heating, and metal reagents.
Article
Chemistry, Multidisciplinary
Wen-Bin Huang, Li-Qi Qiu, Fang-Yu Ren, Liang-Nian He
Summary: The study introduces a straightforward method for the synthesis of alpha-amino phosphine oxides via three-component reactions. The use of aryne to activate formamide simplifies the procedure and offers high efficiency under mild conditions. The mechanistic perception suggests a cascade sequence involving formal [2 + 2] cycloaddition and 1,4-addition reactions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Chang-Hong Liu, Jia-Ming Guo, Xin Li, Jian-Ting Sun, Bang-Guo Wei, Chang-Mei Si
Summary: An efficient method for accessing alpha-arylacetylene-substituted pyrrolidine and piperidine derivatives has been developed using a samarium diiodide-mediated addition-elimination process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xiao-Ping Wang, Yong-Liang Liu, Jie Wei, Ling-Yan Chen, Ya Li
Summary: A diastereoselective Mannich-type reaction between 3-alkyloxindole and N-tert-butanesulfinyl imino ester was reported, providing a concise route to alpha-amino acid derivatives with a specific structural motif. The method is operationally simple and utilizes readily accessible starting materials. A plausible transition-state mode was proposed to explain the observed stereoselectivity in the reaction.
Article
Chemistry, Organic
Yuping Zhu, Tianqi Liu, Bingxin Liu, Houguang Shi, Qitao Tan, Bin Xu
Summary: In this study, alpha-Keto acids were used as novel precursors of nitrile oxides upon treatment with copper nitrate, which reacted with maleimides via [3 + 2] dipolar cycloaddition to form pharmacologically interesting fused isoxazolines. Compared with previous methods, this approach provides a unique and complementary strategy for the convenient synthesis of alkyl substituted nitrile oxides. Mechanistic studies revealed a novel carbon-carbon bond cleavage in alpha-keto acids leading to key gem-dinitroalkane intermediates for the transformation to nitrile oxides in 1,3-dipolar cycloadditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yanjie Wang, Xia Meng, Changqun Cai, Lingyun Wang, Hang Gong
Summary: This study reveals for the first time the cleavage of DMF and electrochemical decarboxylation of alpha-ketoacid under mild conditions, as well as demonstrates the radical cross-coupling reaction between these two electron-deficient radicals. It provides a new electrochemical approach for the cracking of DMF and its application in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yanjie Wang, Xia Meng, Changqun Cai, Lingyun Wang, Hang Gong
Summary: This study reveals for the first time the cleavage of DMF under mild electrochemical conditions and the subsequent reaction of the generated radicals. It provides a safer and milder method for the application of DMF in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hui-Min Wu, Zongpeng Zhang, Liang Wei, Xiu-Qin Dong, Chun-Jiang Wang
Summary: An efficient synthetic methodology was developed to access biologically important and synthetically useful alpha-quaternary cysteine derivatives via asymmetric catalytic alpha-allylation. A wide array of alpha-quaternary cysteine derivatives were obtained with good to excellent enantioselectivities, and gram-scale asymmetric allylation was performed to maintain high yields. Additionally, synthetic transformations to access chiral spirocyclic compounds proceeded smoothly, demonstrating the utility of this methodology.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Ling-Zhi Sun, Xuan Yang, Nan-Nan Li, Meng Li, Qin Ouyang, Jian-Bo Xie
Summary: A facile synthetic method for 4-aryl-4,5-dihydropyrrole-3-carboxylates has been developed using a rhodium-catalyzed ring expansion strategy. This method offers a novel mechanism and enables asymmetric catalytic synthesis with excellent diastereoselectivity, leading to the formation of substituted pyrrolidines.
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.