Article
Chemistry, Organic
Eunjae Chung, Suho Kim, Amitava Rakshit, Pargat Singh, Jaewook Park, Taejoo Jeong, In Su Kim
Summary: In this study, the rhodium(III)-catalyzed C8-spiroannulation of 1-aminonaphthalenes with maleimides is investigated. The resulting C8-alkenylated 1-aminonaphthalenes can further react with nucleophilic 1-amino groups through intramolecular aza-Michael reaction, leading to the formation of spirofused tetracyclic frameworks. This method demonstrates a broad substrate scope and compatibility with various functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Sanjeev Kumar, Saiprasad Nunewar, Srilekha Oluguttula, Srinivas Nanduri, Vinaykumar Kanchupalli
Summary: In the past two decades, transition metal-catalyzed C-H functionalization followed by annulations with various coupling partners has attracted much attention in organic synthesis. Rh(iii) or Ir(iii) catalyzed regioselective C-H functionalization followed by the cyclization of diverse arenes with metal carbene precursors has become a highly investigated research field recently. This review aims to provide a comprehensive essay on the Rh(iii)/Ir(iii) catalyzed C-H functionalizations/annulations via carbene migratory insertion, with a focus on diverse metal carbene precursors with arenes/alkenes reported so far.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shihan Liu, Lei Zhu, Tao Zhang, Kangbao Zhong, Shi-Jun Li, Ruopeng Bai, Yu Lan
Summary: Density functional theory calculations were used to investigate the chemoselectivity of Rh-catalyzed chiral C-F cleavage and gamma-site functionalization. The results indicated that the difference in chemoselectivity in methanol and isobutyronitrile solvents can be attributed to the different controlling steps involved in beta-F elimination and allene insertion. The analysis of explicit solvent models helped explain this discrepancy.
Article
Chemistry, Multidisciplinary
Wei Zhou, Scott R. Docherty, Christian Ehinger, Xiaoyu Zhou, Christophe Coperet
Summary: Rh-based catalysts modified by Mn were studied for CO2 hydrogenation. The addition of Mn shifts the products from pure CH4 to a mixture of methane and oxygenates. In situ XAS confirms the presence of atomically dispersed Mn-II in the vicinity of metallic Rh nanoparticles, which induces the oxidation of Rh to form the Mn-O-Rh interface under reaction conditions. The formed interface is proposed to be key to maintaining Rh+ sites and promoting the formation of CO and alcohols.
Article
Chemistry, Multidisciplinary
Chen-Xu Liu, Fangnuo Zhao, Qing Gu, Shu-Li You
Summary: This paper reports a new method for the enantioselective synthesis of planar chiral ferroceneformaldehydes through a rhodium(I)/phosphoramidite-catalyzed C-H bond arylation reaction. The method enables the efficient synthesis of enantiopure planar chiral ferroceneformaldehydes and their transformation into diverse functional groups.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Organic
Liexin Wu, Liping Li, Haiman Zhang, Hui Gao, Zhi Zhou, Wei Yi
Summary: A unique Rh(III)-catalyzed C-H activation/[3 + 2] annulation of N-phenoxyacetamides has been developed for the construction of dihydrobenzofurans via carbooxygenation of 1,3-dienes. This transformation features a redox-neutral process with specific chemoselectivity, good substrate/functional group compatibility, and profound synthetic potentials. Preliminary exploration for their asymmetric synthesis has been successfully demonstrated, further strengthening the practicality of this approach.
Article
Chemistry, Organic
Liangliang Song, Zhenwei Lv, Yan Li, Kui Zhang, Erik V. Van der Eycken, Lingchao Cai
Summary: In this study, a Rh(III)-catalyzed C-H activation/annulation reaction was developed for the diversification of Lys-based peptides, yielding a range of peptide-isoquinolone conjugates. This method offers racemization-free conditions, high atom and step economy, excellent chemo- and site-selectivity, and broad substrate scope. Furthermore, the peptide-isoquinolone conjugates demonstrate good fluorescent properties and show potential antifungal activity against crop and forest pathogenic fungi, with a particular conjugate exhibiting superior activity compared to the positive control.
Article
Chemistry, Organic
Eric Tan, Leonardo J. Nannini, Otilia Stoica, Antonio M. Echavarren
Summary: The Rh(III)-catalyzed ortho-alkynylation of benzaldehydes is achieved through the transient formation of an imine as a directing group. A wide range of substrates can be obtained under mild reaction conditions, leading to mono- and dialkynylated products. The functionalization of readily available building blocks enables the development of modular syntheses of dibenzopentalenes, isoquinolines, indoles, and indolines.
Article
Chemistry, Multidisciplinary
Chaoying Fang, Li Li, Haitao Yang, Caiyang Kong, Jitan Zhang, Meihua Xie, Jiaping Wu
Summary: Herein, the first highly regio- and chemoselective C2 C-H acyloxylation of indole under rhodium catalysis and an N-quinolinyl auxiliary is presented. This strategy allows for a wide range of indoles and structurally diverse carboxylic acids to yield functionalized indoles with good reaction efficiencies. The utility of this logic is demonstrated by the concise synthesis of functionalized 2-oxindole derivatives. Preliminary mechanistic studies indicate potential involvement of catalyst turnover in this catalytic C-H transformation.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chang-Yun Shi, Xiao-Qu Chen, Ruoqing Zeng, Heng Lu, Zhoulong Fan, Ao Zhang
Summary: This study presents a new approach to difluoroallylation using ruthenium catalysis, which enables the regiodivergent C-H alpha,alpha- and ortho C-H gamma,gamma-difluoroallylation of arenes.
Article
Chemistry, Multidisciplinary
Eike Caldeweyher, Masha Elkin, Golsa Gheibi, Magnus Johansson, Christian Sko''ld, Per-Ola Norrby, John F. Hartwig
Summary: The researchers have developed a hybrid computational model that predicts the site of borylation in complex molecules. The model combines density functional theory, quantum mechanics, cheminformatics, linear regression, and machine learning to accurately predict the major site of borylation in pharmaceutical intermediates, surpassing prior machine-learning models and human experts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Qiao Ren, Ming Lang, Haitao Liu, Xiangyu Li, Daoshun Wu, Jiayun Wu, Meihua Yang, Jianhe Wei, Zhi Ren, Lei Wang
Summary: A rhodium-catalyzed carbene N-H insertion protocol is presented, which enables the simultaneous control of C-N axial and spiro-central chiralities, leading to the rapid synthesis of enantiopure N-arylindolinone-spiroacetal derivatives with high yields and excellent enantioselectivities. This strategy offers promising features, including chiral C-N axis, spiro-central chirality, functional group tolerance, and late-stage diversification. DFT calculations reveal that the N-H insertion step determines the axial chirality, while the 1,5-H shift step is regiospecifically caused by the spirocycle.
Article
Chemistry, Organic
Raju Vaggu, Nagender Thadem, Manda Rajesh, Rene Gree, Saibal Das
Summary: We demonstrate the Rh-catalyzed arene C-H bond alkylation with acylsilane directing group and maleimides. The resulting products are utilized for the synthesis of new tricyclic gamma-lactams through visible-light-induced intramolecular siloxycarbene-amide cyclization. Additionally, we also show the [3 + 2] carbo-annulation of maleimides and aroylsilanes using Ru-catalysis.
Article
Chemistry, Organic
Satabdi Bera, Sanhita Sarkar, Juthi Pal, Rajarshi Samanta
Summary: A rhodium(III)-catalyzed Satoh-Miura type oxidative annulation of N-aryl 2-pyridone derivatives using internal alkyne as a coupling partner is described. The weakly coordinating carbonyl group of the 2-pyridone ring is utilized for this transformation, allowing for a broad scope and wide functional group tolerance. The solvent plays an important role in providing a different class of annulated product. Preliminary investigation of the photophysical properties of the obtained polyarylated N-naphthyl 2-pyridones was also conducted.
Article
Chemistry, Multidisciplinary
Bidhan Ghosh, Satabdi Bera, Pintu Ghosh, Rajarshi Samanta
Summary: An efficient Rh(iii)-catalyzed strategy has been developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp(3)) C-H functionalization, which is mild, simple, regioselective, and tolerates various functional groups with different ring sizes. The method involves C8-methyl metalation, metal-carbene formation, and migratory insertion, with high dilution not necessary and nitrogen being the only byproduct. Preliminary investigation suggests that the C-H metalation step is the rate-determining step.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Victor Mougel, Celine B. Santiago, Pavel A. Zhizhko, Elizabeth N. Bess, Jeno Varga, Georg Frater, Matthew S. Sigman, Christophe Coperet
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Review
Chemistry, Multidisciplinary
Matthew S. Sigman, Kaid C. Harper, Elizabeth N. Bess, Anat Milo
ACCOUNTS OF CHEMICAL RESEARCH
(2016)
Review
Microbiology
Peter Spanogiannopoulos, Elizabeth N. Bess, Rachel N. Carmody, Peter J. Turnbaugh
NATURE REVIEWS MICROBIOLOGY
(2016)
Article
Chemistry, Multidisciplinary
Elizabeth N. Bess, Ryan J. DeLuca, Daniel J. Tindall, Martins S. Oderinde, Jennifer L. Roizen, J. Du Bois, Matthew S. Sigman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Multidisciplinary Sciences
Anat Milo, Elizabeth N. Bess, Matthew S. Sigman
Article
Chemistry, Organic
Elizabeth N. Bess, Matthew S. Sigman
Article
Multidisciplinary Sciences
Elizabeth N. Bess, Amanda J. Bischoff, Matthew S. Sigman
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2014)
Article
Multidisciplinary Sciences
Vayu Maini Rekdal, Elizabeth N. Bess, Jordan E. Bisanz, Peter J. Turnbaugh, Emily P. Balskus
Article
Microbiology
Rachel N. Carmody, Jordan E. Bisanz, Benjamin P. Bowen, Corinne F. Maurice, Svetlana Lyalina, Katherine B. Louie, Daniel Treen, Katia S. Chadaideh, Vayu Maini Rekdal, Elizabeth N. Bess, Peter Spanogiannopoulos, Qi Yan Ang, Kylynda C. Bauer, Thomas W. Balon, Katherine S. Pollard, Trent R. Northen, Peter J. Turnbaugh
NATURE MICROBIOLOGY
(2019)
Article
Microbiology
Elizabeth N. Bess, Jordan E. Bisanz, Fauna Yarza, Annamarie Bustion, Barry E. Rich, Xingnan Li, Seiya Kitamura, Emily Waligurski, Qi Yan Ang, Diana L. Alba, Peter Spanogiannopoulos, Stephen Nayfach, Suneil K. Koliwad, Dennis W. Wolan, Adrian A. Franke, Peter J. Turnbaugh
NATURE MICROBIOLOGY
(2020)
Article
Biology
Vayu Maini Rekdal, Paola Nol Bernadino, Michael U. Luescher, Sina Kiamehr, Chip Le, Jordan E. Bisanz, Peter J. Turnbaugh, Elizabeth N. Bess, Emily P. Balskus
Article
Microbiology
Jordan E. Bisanz, Paola Soto-Perez, Cecilia Noecker, Alexander A. Aksenov, Kathy N. Lam, Grace E. Kenney, Elizabeth N. Bess, Henry J. Haiser, Than S. Kyaw, Feiqiao B. Yu, Vayu M. Rekdal, Connie W. Y. Ha, Suzanne Devkota, Emily P. Balskus, Pieter C. Dorrestein, Emma Allen-Vercoe, Peter J. Turnbaugh
CELL HOST & MICROBE
(2020)
Editorial Material
Microbiology
Lizett Ortiz de Ora, Elizabeth N. Bess
Summary: This commentary discusses the impact of gut microbiome on neuronal functions and highlights Caenorhabditis elegans as a valuable model for studying this interaction. With a fully mapped neuronal circuitry, C. elegans is an effective tool for studying nervous system signaling with translational relevance to human disease. The routine use of gnotobiotic C. elegans for examining the gut-brain axis is envisioned to aid in the development of novel therapeutic interventions for brain diseases.
Article
Biotechnology & Applied Microbiology
Barry E. Rich, Jayme C. Jackson, Lizett Ortiz de Ora, Zane G. Long, Kylie S. Uyeda, Elizabeth N. Bess
Summary: This study identified gut bacteria capable of synthesizing dopamine from 3MT through O-demethylation, potentially impacting dopamine regulation.
JOURNAL OF APPLIED MICROBIOLOGY
(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.
