Article
Chemistry, Multidisciplinary
Ndidi U. N. Iwumene, Daniel F. Moseley, Robert D. C. Pullin, Michael C. Willis
Summary: Rhodium-catalyzed hydroacylation reactions can be used to synthesize linear α,β-unsaturated enone intermediates, which can be used to construct diverse substituted saturated O-, N-, and S-heterocycles in a one-pot process. The reaction conditions can be adjusted to selectively form O-heterocycles with high levels of diastereoselectivity.
Article
Chemistry, Multidisciplinary
Emilie Wheatley, Joseph M. Zanghi, Miles M. Mason, Simon J. Meek
Summary: A practical method is presented for the preparation of versatile ketones and aldehydes containing an alpha-quaternary stereocenter. The method utilizes simple starting materials and a chiral phosphine catalyst, and provides a variety of substituted ketone and aldehyde products in good yield and high enantiomeric excess. The reactions proceed via acyl substitution with chiral allylic nucleophiles, and show selectivity and conversion dependence on a protic additive. The utility of this approach is demonstrated through several product transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Jiang-Fei Li, Wei-Wei Xu, Rong-Hua Wang, Yue Li, Ge Yin, Mengchun Ye
Summary: The study demonstrates a novel approach for the direct construction of 7-membered rings via Ni-Al co-catalyzed unreactive C-H cyclization of benzoimidazoles with alkenes, yielding a series of tricyclic imidazoles. Transition metal-catalyzed C-H cyclization for medium-ring synthesis has been limited to reactive C-H bonds, presenting a challenge for activating unreactive C-H bonds.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Peng-Ying Jiang, San Wu, Guan-Jun Wang, Shao-Hua Xiang, Bin Tan
Summary: QUINAPs are a crucial class of chiral compounds that have remarkable features in stereoinduction. However, their restricted substrate range and expensive price limit their broader utilization. In this study, the first atroposelective oxidation of an N atom using a chiral ketone catalyst was described, allowing the kinetic resolution of QUINAPOs with excellent enantioselectivity. Mechanistic investigations revealed the role of a dioxirane as the active catalytic species. The developed protocol has practicality and can be applied in enantioselective transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Peng-Ying Jiang, San Wu, Guan-Jun Wang, Shao-Hua Xiang, Bin Tan
Summary: QUINAPs have been widely used in enantioselective transformations, but their limited substrate range and high cost hinder their broader application. In this study, we report the first atroposelective oxidation of an N atom using a chiral ketone catalyst, allowing the kinetic resolution of QUINAPOs with excellent enantioselectivity. The enantioenriched products can be easily converted into the desired QUINAP targets without loss of stereochemical integrity. Mechanistic investigations reveal the involvement of a dioxirane as the active catalytic species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jun Sato, Kenji Yamawaki, Takuya Oguma
Summary: Here we report a stereoselective synthesis method for the tricyclic beta-lactam core, which is obtained from an accessible and inexpensive commercially available cephalosporin intermediate through sulfoxide-directed oxidative lactonization in six steps, with a total yield of 23%.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Guoxue He, Jinyu Ma, Jianhui Zhou, Chunpu Li, Hong Liu, Yu Zhou
Summary: A new method for synthesizing indanones using L-proline as a catalyst under metal- and additive-free conditions has been developed, providing a more environmentally friendly pathway with good yields. This method can be used to synthesize the anti-AD drug donepezil.
Article
Chemistry, Organic
Golla Ramesh, Rengarajan Balamurugan
Summary: An efficient protocol for the synthesis of indole-substituted indanes from o-alkenylbenzaldehydes under acetalization conditions has been presented. The cyclization occurs through nucleophilic addition of indole followed by a conrotatory 4 pi-electrocyclization reaction, ensuring exclusive diastereoselectivity. The olefin geometry of o-alkenylbenzaldehyde and the amount of indole are crucial factors for the success of this cyclization process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Heng Zhang, Xiaoyan Lv, Hanrui Yu, Zibo Bai, Gong Chen, Gang He
Summary: A new protocol has been developed for amide-directed Cu-catalyzed aminoalkylation of unactivated alkenes using cyclobutanone oxime esters as alkyl radical donors. Both primary and secondary alkyl groups can be selectively installed at the C4 position of terminal or cis-internal 3-alkenamides in moderate to good yield. The use of a weakly coordinating counteranion as the Cu catalyst is critical for the formation of beta-lactam products.
Article
Chemistry, Multidisciplinary
Ryan E. McNamee, Marius M. Haugland, Jeremy Nugent, Rachel Chan, Kirsten E. Christensen, Edward A. Anderson
Summary: BCBs are important intermediates for the synthesis of various four-membered and bicyclo[1.1.1]pentane derivatives, but variations in bridgehead substituents can be challenging due to the inherent strain of the bicyclic scaffold. This study reports the first palladium-catalyzed cross-coupling on pre-formed BCBs, enabling late-stage diversification of the bridgehead position.
Article
Chemistry, Physical
Sangwon Seo, Ming Gao, Eva Paffenholz, Michael C. Willis
Summary: This study demonstrates that aryltriazenes can promote three distinctive types of C-H functionalization reactions, allowing the preparation of complex benzene molecules with diverse substitution patterns. The resulting products can undergo further derivatization providing traceless outcomes, providing a new method for the synthesis of complex organic molecules.
Article
Chemistry, Multidisciplinary
Rodney A. Fernandes, Dnyaneshwar A. Gorve, Amit K. Jha
Summary: A stereodivergent protecting-group-directed Tsuji-Trost cyclization has been successfully used to synthesize both 2,5-cis- and 2,5-trans-disubstituted-THF scaffolds. In the presence of a beta-O-silyl group, cis-2,5-disubstituted-3-oxygenated THF is formed with a high diastereomeric ratio of up to 9:1. Alternatively, when the free OH at the beta-position can coordinate with acetate, trans-2,5-disubstituted-3-hydroxy THF scaffold is generated as a single diastereomer (diastereomeric ratio up to 1:0). These THF scaffolds were used in the total synthesis of oxylipids and (+)-petromyroxol.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Thomas Varlet, Damien Bouchet, Elsa Van Elslande, Geraldine Masson
Summary: A convenient and scalable dearomative hydroacylation reaction of indoles is reported. Using readily available aldehydes as acyl sources and TBADT as an inexpensive direct HAT photocatalyst, various indole derivatives are converted into synthetically interesting 2-acylindolines with good yields and diastereoselectivity under mild conditions. An asymmetric version of the reaction is successfully developed, and an experimental mechanistic investigation provides further insights into the assumed reaction pathway.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Cong Shen, Yuhang Zhu, Wenzhou Shen, Shuqi Jin, Guofu Zhong, Shuxin Luo, Lixia Xu, Liangjun Zhong, Jian Zhang
Summary: An efficient method for the preparation of aryl 1,3-dienes from styrenes and olefins has been developed, utilizing a transient chiral auxiliary derived from aldehydes. The generality of this protocol was demonstrated by the smooth conversion of various 2-vinyl benzaldehyde derivatives, resulting in high yields and excellent enantioselectivities. The derived axially chiral carboxylic acid was found to be a more efficient ligand in the Cp*Co(iii)-catalyzed asymmetric C(sp(3))-H alkylation.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Engineering, Chemical
Jiandong Zhang, Rui Dong, Xiaoxiao Yang, Lili Gao, Chaofeng Zhang, Fan Ren, Jing Li, Honghong Chang
Summary: In this study, four new bacterial DDHs were discovered and used to catalyze the oxidation reaction for the preparation of enantiopure vicinal diols. Among them, HcDDH showed high catalytic activity and potential for the synthesis of a broad range of chiral vicinal diols.
CHINESE JOURNAL OF CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Applied
Kevin G. M. Kou, Lauren E. Longobardi, Vy M. Dong
ADVANCED SYNTHESIS & CATALYSIS
(2015)
Article
Multidisciplinary Sciences
C. J. Marth, G. M. Gallego, J. C. Lee, T. P. Lebold, S. Kulyk, K. G. M. Kou, J. Qin, R. Lilien, R. Sarpong
Article
Chemistry, Organic
K. G. M. Kou, V. M. Dong
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Jung-Woo Park, Kevin G. M. Kou, Daniel K. Kim, Vy M. Dong
Article
Chemistry, Multidisciplinary
Kevin G. M. Kou, Beryl X. Li, Jack C. Lee, Gary M. Gallego, Terry P. Lebold, Antonio G. DiPasquale, Richmond Sarpong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
Kevin G. M. Kou, Svitlana Kulyk, Christopher J. Marth, Jack C. Lee, Nicolle A. Doering, Beryl X. Li, Gary M. Gallego, Terry P. Lebold, Richmond Sarpong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Ken Mukai, Danilo Pereira de Sant'Ana, Yasuo Hirooka, Eduardo V. Mercado-Marin, David E. Stephens, Kevin G. M. Kou, Sven C. Richter, Naomi Kelley, Richmond Sarpong
Article
Chemistry, Multidisciplinary
Kevin G. M. Kou, Jason J. Pflueger, Toshihiro Kiho, Louis C. Morrill, Ethan L. Fisher, Kyle Clagg, Terry P. Lebold, Jessica K. Kisunzu, Richmond Sarpong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Organic
Nicolle A. Doering, Kevin G. M. Kou, Krissada Norseeda, Jack C. Lee, Christopher J. Marth, Gary M. Gallego, Richmond Sarpong
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Peter K. Dornan, Kevin G. M. Kou, K. N. Houk, Vy M. Dong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Physical
Xuezhen Kou, Kevin G. M. Kou
Correction
Chemistry, Physical
Xuezhen Kou, Kevin G. M. Kou
Article
Chemistry, Organic
Robert Crowley III, Berkley Lujan, Alex Martinez, Roni Manasi, Justin D. Debow, Kevin G. M. Kou
Summary: This article presents a method for manipulating carbon-centered radicals to react with electron-deficient systems. By coupling the Fe(II)-mediated Fenton reaction with the Fe(III)-mediated single-electron oxidation of anisolic compounds, the electron-rich carbon-centered radicals can react with electron-rich arenes, resulting in the production of diarylmethane derivatives from simple unfunctionalized precursors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Aaron Pan, Maja Chojnacka, Robert Crowley, Lucas Gottemann, Brandon E. Haines, Kevin G. M. Kou
Summary: This study presents a new dual acid catalyst system involving environmentally benign and readily accessible protic acid and iron for the site-selective tert-butylation of electron-rich arenes. It also develops a synergistic Bronsted/Lewis acid catalyzed aromatic alkylation, filling a gap in the Friedel-Crafts reaction literature. The use of non-allylic, non-benzylic, and non-propargylic tertiary alcohols is explored, leading to the formation of new quaternary carbon centers.
Review
Chemistry, Organic
Viviene K. Nguyen, Kevin G. M. Kou
Summary: This mini-review provides a concise overview of the biosynthetic pathway and pharmacology of bisbenzylisoquinoline alkaloid natural products, with additional emphasis on methodologies in total syntheses of simpler acyclic diaryl ether dimers and their macrocyclic counterparts.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
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.
