Article
Chemistry, Multidisciplinary
Mukesh Pappoppula, Kathryn L. Olsen, Devin R. Ketelboeter, Aaron Aponick
Summary: A highly enantioselective alkynylation of pyridine is reported. The reaction is enabled by StackPhos and proceeds with excellent regioselectivity (25 : 1), enantioselectivity (up to 99 % ee), and yield (up to 99 %). Terminal alkynes with a wide range of functional groups work well in the transformation, including acetylene gas, paving the way for the use of these feedstock starting materials to rapidly access highly useful synthetic intermediates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shuai Zhang, Nan Jiang, Jun-Zhao Xiao, Guo-Qiang Lin, Liang Yin
Summary: Herein, a copper(I)-catalyzed asymmetric hydrophosphination method for 3,3-disubstituted cyclopropenes is reported. The method provides phosphine derivatives with high diastereo- and enantioselectivities. It has a broad substrate scope and the high stereoselectivity is attributed to the stability and asymmetric induction of the Cu(I)-(R,R)-QUINOXP* complex. The method is also used for the synthesis of new chiral phosphine-olefin compounds, which serve as ligands in Rh-catalyzed asymmetric conjugate addition reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shuai Zhang, Nan Jiang, Jun-Zhao Xiao, Guo-Qiang Lin, Liang Yin
Summary: A copper(I)-catalyzed asymmetric hydrophosphination of 3,3-disubstituted cyclopropenes is reported, providing a range of highly selective phosphine derivatives. The method shows broad substrate scope and the high stereoselectivity is attributed to the stability of the Cu(I)-(R,R)-QUINOXP* complex and its asymmetric induction. Finally, the method is used for the synthesis of new chiral phosphine-olefin compounds, one of which serves as a wonderful ligand in Rh-catalyzed asymmetric conjugate addition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Zhen Yang, Peiyuan Li, Hongjian Lu, Guigen Li
Summary: The enantioselective copper-catalyzed borylacylation of aryl olefins with acyl chlorides and bis-(pinacolato)diboron is an efficient and versatile method to synthesize chiral beta-borylated ketones with potential applications in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yan-Bo Li, Hu Tian, Shuai Zhang, Jun-Zhao Xiao, Liang Yin
Summary: In this study, a copper(I)-catalyzed reaction of diarylphosphines and O-benzoyl hydroxylamines was developed, leading to the synthesis of aminophosphinites and P-chiral aminophosphinites. The reaction mechanism was proposed and further transformation to P-chiral phosphines was achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tatiana Suarez-Rodriguez, Angel L. Suarez-Sobrino, Alfredo Ballesteros
Summary: Gold(I)-catalyzed higher-order [8+2] cycloadditions of 8-aryl-8-azaheptafulvenes with allenamides and ynamides were studied, resulting in the formation of 1,8-dihydrocycloheptapyrroles and 2-amido-1,4-dihydrocycloheptapyrroles, respectively. The reactions proceeded with good yields and various substituents, suggesting a nucleophilic attack mechanism involving the gold-activated electron-rich moieties of the allenamide and ynamide.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Yuqi Zhu, Ting Zhou, Hong Zhang, Jieyin He, Hongguang Li, Ming Lang, Jian Wang, Shiyong Peng
Summary: This study reports a Rh(II)-catalyzed reaction method for the synthesis of α-aryl-β-aminocyclopropane carboxylic acid derivatives with stereo-isomeric centers using donor-acceptor carbenes derived from a-aryldiazoesters and vinylsulfonamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Si-Qing Wang, Zong-Ci Liu, Wen-Jun Yue, Liang Yin
Summary: This study reveals a vinylogous aldol-type reaction for the synthesis of chiral gamma-hydroxyl-alpha,beta-unsaturated azaarenes with high selectivity and yields. The use of different ligands can control the formation of the carbon-carbon double bond in the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qile Wang, Thomas R. Hoye
Summary: The study presents a novel Cu(I)-catalyzed reaction for introducing different substituents onto benzyne molecules, showing potential for various applications.
Article
Chemistry, Organic
Jun-An Xiao, Hai Peng, Huan Zhang, Ru-Fang Meng, Chenxiang Lin, Wei Su, Yanmin Huang
Summary: The diastereoselective assembly of spiroindolenines through a synergistic scandium/gold-catalyzed dearomative spiroannulation is presented. This protocol provides access to a wide range of spiroindolenine derivatives with an average yield of 86%, exhibiting moderate to excellent diastereoselectivities (up to 97:3 dr). Experimental studies support the feasibility of bimetallic relay catalysis, and the scale-up reaction and synthetic transformations of the spiroindolenine product demonstrate its synthetic utility.
Article
Chemistry, Multidisciplinary
Zhi-Zhou Pan, Jia-Heng Li, Hu Tian, Liang Yin
Summary: A copper(I)-catalyzed asymmetric allylation of ketones with 2-aza-1,4-dienes has been demonstrated, providing a series of functionalized homoallyl tertiary alcohols with high to excellent enantioselectivity. The deprotonation of N-allyl-1,1-diphenylmethanimines is the rate-determining step in the reaction, generating nucleophilic allyl copper(I) species. The utility of this method has been demonstrated by the asymmetric synthesis of (R)-boivinianin A and (R)-gossonorol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yan Ban, Yingxin Wang, Hao Li, Yan Wang, Dianjun Li, Jinhui Yang
Summary: The first Ir(i)-catalyzed thioamide-assisted C-H arylation of ferrocenes with aryl boronic acids under base-free mild reaction conditions in the presence of Ag2CO3 as an oxidant with eco-friendly 2-MeTHF as a solvent was developed. This reaction exhibits a broad substrate scope (37 examples) and excellent functional group tolerance (yields ranging from 18% to 94%), offering a promising approach to the synthesis of aryl thioamide-ferrocene compounds with high yields and regioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yue Jia, Zhihan Zhang, Guo-Ming Yu, Xuan Jiang, Liang-Qiu Lu, Wen-Jing Xiao
Summary: A visible light induced enantioselective deaminative arylation of amino acid derivatives by bifunctional copper catalysis is disclosed. A variety of alpha-aryl-N-phenylamides are prepared with good efficiency and high enantioselectivity. Experimental investigations and theoretical calculations reveal the crucial role of additional phenols in improving catalytic efficiency and enantiocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Manikantha Maraswami, Hajime Hirao, Teck-Peng Loh
Summary: This study achieved meta-arylation of phenols through copper catalysis with complete meta-selectivity and good tolerance towards various functional groups. Computational studies revealed that the reaction proceeded via a Heck-like pathway.
Article
Chemistry, Physical
Xiaodong Ma, Guozhu Zhang
Summary: This study describes a copper-catalyzed, highly enantioselective alkyl and aryl/azolation of alkenes, where the use of a specific chiral ligand plays a crucial role in the success of the chemistry. Anionic tridentate ligands are employed to enhance the reducibility of copper complexes, facilitating the generation of alkyl/aryl radicals and providing good enantiocontrol in the azolation. The three-component coupling reactions have mild reaction conditions and can tolerate a broad range of functional groups, allowing for the straightforward introduction of valuable azole functionalities into complex molecular systems through direct C-H functionalization.
Article
Chemistry, Applied
Laure Peilleron, Pascal Retailleau, Kevin Cariou
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Inorganic & Nuclear
Sarah Keller, Yih Ching Ong, Yan Lin, Kevin Cariou, Gilles Gasser
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2020)
Review
Chemistry, Applied
Capucine Mahe, Kevin Cariou
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Multidisciplinary
Loic Habert, Kevin Cariou
Summary: In this study, the aerobic iodoarene catalysis was achieved by using a pyrylium photocatalyst under blue light irradiation, allowing for the use of low catalytic loading of both catalysts under very mild operating conditions. This unprecedented dual organocatalytic system provides a powerful and efficient methodology for spiro-cyclization of amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Agathe C. A. D'Hollander, Eugenie Romero, Kamsana Vijayakumar, Camille Le Houerou, Pascal Retailleau, Robert H. Dodd, Bogdan I. Iorga, Kevin Cariou
Summary: In this study, it was found that ynamides can undergo a [3+2] cycloaddition with 2-azaallyl anions under basic conditions and heat, resulting in the formation of nitrogen-rich heterocycles. The reaction generally shows excellent diastereoselectivity, favoring the cis adduct. Deuteration experiments and DFT calculations were used to rationalize the regio- and stereoselectivity of the process as well as the formation of side products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Medicinal
Eugenie Romero, Saoussen Oueslati, Mohamed Benchekroun, Agathe C. A. D. Hollander, Sandrine Ventre, Kamsana Vijayakumar, Corinne Minard, Cynthia Exilie, Linda Tlili, Pascal Retailleau, Agustin Zavala, Eddy Elisee, Edithe Selwa, Laetitia A. Nguyen, Alain Pruvost, Thierry Naas, Bogdan I. Iorga, Robert H. Dodd, Kevin Cariou
Summary: A series of imino-analogues of beta-lactams have been developed as efficient non-covalent inhibitors of beta-lactamases, showing inhibitory effects on three major carbapenemases and a cephalosporinase.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Lisa Gourdon, Kevin Cariou, Gilles Gasser
Summary: Photodynamic therapy and photoactivated chemotherapy are therapeutic techniques that utilize photosensitizers and light to control drug activation. Exploration of first-row transition metal complexes as photosensitizers has shown promising results.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Maria Gil-Moles, Sebastian Tuerck, Uttara Basu, Andrea Pettenuzzo, Saurav Bhattacharya, Ananthu Rajan, Xiang Ma, Rolf Buessing, Jessica Woelker, Hilke Burmeister, Henrik Hoffmeister, Pia Schneeberg, Andre Prause, Petra Lippmann, Josephine Kusi-Nimarko, Storm Hassell-Hart, Andrew McGown, Daniel Guest, Yan Lin, Anna Notaro, Robin Vinck, Johannes Karges, Kevin Cariou, Kun Peng, Xue Qin, Xing Wang, Joanna Skiba, Lukasz Szczupak, Konrad Kowalski, Ulrich Schatzschneider, Catherine Hemmert, Heinz Gornitzka, Elena R. Milaeva, Alexey A. Nazarov, Gilles Gasser, John Spencer, Luca Ronconi, Ulrich Kortz, Jindrich Cinatl, Denisa Bojkova, Ingo Ott
Summary: The global spread of SARS-CoV-2 has highlighted the need for antiviral therapeutics, with studies showing potential activity of metal complexes, including gold, silver, and POMs, in inhibiting the replication mechanisms of the virus.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Capucine Mahe, Agathe C. A. D'Hollander, Kevin Cariou
Summary: Under basic conditions, N-arylketenimines can be generated from N-Boc ynamides and react with various hydrazones, leading to the formation of acetimidohydrazides.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Robin Vinck, Albert Gandioso, Pierre Burckel, Bruno Saubamea, Kevin Cariou, Gilles Gasser
Summary: Four new ruthenium(II) polypyridyl complexes were synthesized and their properties were studied. It was found that these complexes could self-assemble into nanoparticles and accumulate in lysosomes upon internalization by cells. Conjugation with biotin increased cellular uptake but did not increase phototoxicity. However, these complexes showed high phototoxicity upon irradiation at long wavelengths (645-670 nm) and self-assembling behavior, making them promising for the development of new lysosome-targeted photosensitizers for photodynamic therapy.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Robin Vinck, Johannes Karges, Mickael Tharaud, Kevin Cariou, Gilles Gasser
Summary: Eight new ruthenium complexes were synthesized by modifying ligands or changing metal coordination, and their effects on physical, spectroscopic, and biological properties were studied. The modifications had moderate effects on visible light absorption and singlet oxygen quantum yield, but significant impacts on lipophilicity, cellular uptake, and phototoxicity. This work identified two promising ruthenium complexes as photosensitizers for photodynamic therapy and provided guidance for designing better photosensitizers.
DALTON TRANSACTIONS
(2021)
Review
Chemistry, Multidisciplinary
Yan Lin, Harley Betts, Sarah Keller, Kevin Cariou, Gilles Gasser
Summary: This review explores the potential of metal-based antifungal agents in improving bioavailability and treating fungal infections by combining organic moieties with metal ions. Additionally, coordination of metal ions can expand the library of antifungal drugs available, providing more treatment options for medical professionals.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Biochemistry & Molecular Biology
Riccardo Rubbiani, Tobias Weil, Noemi Tocci, Luciano Mastrobuoni, Severin Jeger, Marco Moretto, James Ng, Yan Lin, Jeannine Hess, Stefano Ferrari, Andres Kaech, Luke Young, John Spencer, Anthony L. Moore, Kevin Cariou, Giorgia Renga, Marilena Pariano, Luigina Romani, Gilles Gasser
Summary: Fungal infections pose a global threat, especially for immunocompromised patients. The study focused on developing and characterizing novel organometallic derivatives of the frontline antifungal drug fluconazole, with one derivative showing significantly higher antifungal activity than fluconazole and effectiveness against clinical isolates. This finding highlights the potential of organometallic compounds in combating fungal infections and drug resistance.
RSC CHEMICAL BIOLOGY
(2021)
Article
Chemistry, Inorganic & Nuclear
Yan Lin, Yih Ching Ong, Sarah Keller, Johannes Karges, Rafika Bouchene, Eric Manoury, Olivier Blacque, Joachim Mueller, Nicoleta Anghel, Andrew Hemphill, Cecile Haberli, Aya C. Taki, Robin B. Gasser, Kevin Cariou, Jennifer Keiser, Gilles Gasser
DALTON TRANSACTIONS
(2020)
Review
Chemistry, Organic
Laure Peilleron, Kevin Cariou
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
