Article
Chemistry, Multidisciplinary
Yang Yuan, Youcan Zhang, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: A novel method for constructing amide bonds through anti-Markovnikov hydroaminocarbonylation of unactivated alkenes has been developed. Copper catalysis, hydroxylamine electrophile reagents, and poly(methylhydrosiloxane) (PMHS) were used under mild conditions. The reaction showed a high degree of tolerance towards various functional groups and efficiently converted unactivated terminal alkenes, 1,1-disubstituted alkenes, and cyclic alkenes to the corresponding amides with exclusive anti-Markovnikov selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yang Yuan, Youcan Zhang, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: This paper reports a general method for the anti-Markovnikov hydroaminocarbonylation of unactivated alkenes under mild conditions, using copper catalysis in combination with hydroxylamine electrophile reagents and poly(methylhydrosiloxane) (PMHS) as a cheap and environmentally friendly hydride source. The reaction tolerates a variety of functional groups and efficiently converts unactivated terminal alkenes, 1,1-disubstituted alkenes, and cyclic alkenes to the corresponding amides with exclusive anti-Markovnikov selectivity (and high enantioselectivities/diastereoselectivities). Additionally, with minimal modification of the reaction conditions, alkynes can also undergo tandem hydrogenation-hydroaminocarbonylation to alkyl amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Pin Ding, Lingbo Han, Jiaxing Bai, Jingjing Liu, Xinjun Luan
Summary: The study introduces an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation for assembling synthetically useful carbazoles in one step. The key to the success of this reaction lies in the careful selection of amino sources and Pd(0) catalysts.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Benxiang Zhang, Jiayan He, Yi Li, Tao Song, Yewen Fang, Chaozhong Li
Summary: Acylphosphonates with the 5,5-dimethyl-1,3,2-dioxophosphinanyl skeleton have been developed as efficient intermolecular radical acylation reagents for cobalt-catalyzed Markovnikov hydroacylation of unactivated alkenes at room temperature. The protocol shows broad substrate scope and good functional group compatibility, providing satisfactory yields of branched ketones. The proposed mechanism involves Co-H mediated hydrogen atom transfer and subsequent trapping of alkyl radicals by acylphosphonates.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Mingda Li, Yangbin Jin, Yupeng Chen, Wanqing Wu, Huanfeng Jiang
Summary: This paper reports a new catalytic system for the efficient oxidative amination of unactivated olefins with primary aliphatic amines, leading to the formation of secondary allylic amines. The reaction proceeds through allylic C(sp3)-H activation and nucleophilic amination. The utility of this method is demonstrated in the late-stage modification and streamlined synthesis of drug molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Tao Song, Kuiyang Wang, Qianjia Yuan, Wanbin Zhang
Summary: This study reports the nickel-catalyzed hydroamination and hydroalkoxylation reactions between unactivated amines and alcohols with enolactams. The method demonstrates good functional group tolerance and delivers the corresponding hydrofunctionalized products in good to excellent yields (& LE;98%). Additionally, an intramolecular hydroalkoxylation of an enolactam is successfully achieved, providing a cyclization product in good yield. Mechanistic studies reveal that tBuI plays crucial roles as a hydride donor and radical precursor for the reaction's success.
Article
Chemistry, Physical
Satavisha Sarkar, Arghya Banerjee, Ming-Yu Ngai
Summary: In this study, a new metal-catalyzed reaction was developed to synthesize ketonylated carbocycles with important biological activities. The reaction offers simple operation, mild reaction conditions, and tolerance towards various functional groups.
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Laura Talavera, Robert R. A. Freund, Huihui Zhang, Matthew Wakeling, Mara Jensen, Ruben Martin
Summary: In this study, a novel Ni-catalyzed 1,1-difunctionalization reaction of unactivated terminal alkenes is disclosed, allowing for the incorporation of two different heteroatom motifs across an olefin backbone. This method provides a streamlined approach to the synthesis of alpha-aminoboronic acid derivatives from simple precursors and exhibits simplicity and generality across a wide range of coupling counterparts.
Article
Chemistry, Organic
Chikkabagilu Nagaraju Shambhavi, Masilamani Jeganmohan
Summary: A Ru(II)-catalyzed weak chelating group-aided ortho-C-H alkylation of arylamides with unactivated olefins in a redox-neutral fashion was demonstrated. This reaction was suitable for various substituted arylamides and unactivated aliphatic alkenes, with pivalic acid playing a dual role.
Article
Chemistry, Physical
Laura Talavera, Robert R. A. Freund, Huihui Zhang, Matthew Wakeling, Mara Jensen, Ruben Martin
Summary: Here, a novel Ni-catalyzed 1,1-difunctionalization of unactivated terminal alkenes is disclosed, allowing for the incorporation of two different heteroatom motifs across an olefin backbone. This streamlines the access to alpha-aminoboronic acid derivatives from simple precursors, and the method exhibits simplicity and generality across a wide range of coupling counterparts.
Article
Chemistry, Organic
Lu-Wen Zhang, Xiao-Jun Deng, Dong-Xu Zhang, Qin-Qin Tian, Wei He
Summary: This study introduces a novel method for the synthesis of amino lactones and explores the influence of the iodoarene precatalyst structure on reaction rate, demonstrating its selective adjustment effect in aminolactonization and oxylactonization. Furthermore, the feasibility of asymmetric aminolactonization catalyzed by a chiral iodoarene precatalyst was verified through preliminary experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Yiting Hao, Xinlin Wang, Yumeng Wu, Liangliang Song, Kui Zhang, Lingchao Cai
Summary: A concise and modular method for the synthesis of chiral organic compounds bearing pyridyl-substituted stereogenic centers has been established. The method enables the introduction of stereogenic C-(sp(3)) centers into widely available alkenes via a nickel/Box catalyst with alpha-pyridyl alkyl bromide. The reaction conditions are mild and allow for a wide substrate scope and good functional-group tolerance, resulting in the formation of various enantioenriched alkylated pyridine derivatives with high yields and enantioselectivities. Further application of enantioenriched pyridine derivatives is demonstrated through an asymmetric Si-H bond insertion reaction, showcasing the productive utility of this modular strategy.
Article
Chemistry, Multidisciplinary
Tao Zhong, Ji-Tao Yi, Zhi-Da Chen, Quan-Can Zhuang, Yong-Zhao Li, Gui Lu, Jiang Weng
Summary: This study successfully reported the first three-component aminofluorosulfonylation of unactivated olefins by merging photoredox-catalyzed proton-coupled electron transfer (PCET) activation with radical relay processes, efficiently affording various aliphatic sulfonyl fluorides featuring a privileged 5-membered heterocyclic core under mild conditions with good functional group tolerance. The synthetic potential of the sulfonyl fluoride products was examined by diverse transformations including SuFEx reactions and transition metal-catalyzed cross-coupling reactions, with mechanistic studies demonstrating the involvement of amidyl radicals, alkyl radicals, and sulfonyl radicals in this difunctionalization transformation.
Article
Chemistry, Applied
Hui-Min Jiang, Qing Sun, Jin-Peng Jiang, Jing-Hao Qin, Xuan-Hui Ouyang, Ren-Jie Song
Summary: We have described a method for the dicarbofunctionalization of alkenes, which allows for the introduction of alkyl and electron-rich aryl groups across the C=C bond of styrenes. This is achieved under copper catalyst and oxidative conditions, resulting in the construction of C(sp(3))-C(sp(2))/C(sp(3))-C(sp(3)) bonds via dual C-H functionalization. The method enables the synthesis of 1,1-diarylalkanes, which are important scaffolds found in natural products and drug molecules, by grafting electron-rich aromatics such as indoles, pyrroles, and trisubstituted aromatics.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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.