Article
Chemistry, Organic
Sebastien G. Guillet, Aleksei A. Logvinov, Vladislav A. Voloshkin, Ekaterina A. Martynova, Steven P. Nolan
Summary: Researchers report a simple method for the synthesis of azetidines from 2-isoxasoline-3-carboxylates and alkenes, using [Au(cbz)(NHC)] complexes as photocatalysts. The reaction is applicable to a wide range of substrates. Mechanistic studies confirm the energy transfer pathway. This study further expands the potential application of gold catalysts in energy transfer chemistry and catalysis.
Article
Chemistry, Multidisciplinary
Jianyang Dong, Fuyang Yue, Jianhua Liu, Hongjian Song, Yuxiu Liu, Qingmin Wang
Summary: The described Minisci reaction allows for the catalytic synthesis of heteroarylethyl alcohols by sequentially adding H2O and N-heteroarenes across olefinic double bonds. This scalable protocol enables direct hydroxy-heteroarylation of olefins with a wide range of N-heteroarenes and has the potential to rapidly convert abundant feedstock materials into medically relevant molecules.
Article
Chemistry, Multidisciplinary
Lanfeng Wei, Yu Wei, Jinli Zhang, Liang Xu
Summary: This research explores a visible-light-induced oxidative dehydrogenative process using an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant. This approach successfully accessed an array of N-heterocycles under metal-free mild conditions, in good to excellent yields.
Article
Chemistry, Applied
Jiacheng Li, Suan Siang Tan, Sara Helen Kyne, Philip Wai Hong Chan
Summary: A synthetic method for the Hantzsch ester-mediated C2-alkylation of quinolines, isoquinolines, and pyridines using N-(acyloxy)phthalimide esters (NHPI) under blue LED light has been described. The metal-free protocol provides alkylated N-heterocyclic products with high yields and can be carried out at room temperature. The introduction of a chiral phosphoric acid enables an asymmetric version of the reaction with high enantiomeric excess values. The reaction mechanism involves the excitation of an electron-donor acceptor complex and the addition of a radical species to the N-heterocycle.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Xinyan Lv, Yaohang Cheng, Yingxiao Zong, Qingyun Wang, Guanghui An, Junke Wang, Guangming Li
Summary: In this study, a visible-light-mediated Ru-catalyzed para-alkylation of anilines was reported. The reaction showed high efficiency and mild conditions, with good functional group tolerance for late-stage functionalization of natural products and drugs.
Article
Chemistry, Multidisciplinary
Zhengyi Pan, Qian Zhang, Wenquan Wang, Lulin Wang, Guang-Hui Wang
Summary: In this study, a facile strategy was developed to synthesize two carbon-doped Ni catalysts, which can switch the selectivity in the reductive amination of biomass-derived carbonyl compounds and exhibit excellent stability and a broad substrate scope.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Physical
Dongdong Lv, Yaru Li, Wei Qiao, Dongdong Zhang, Yuanqiang Mai, Nengjun Cai, Hongwei Xiang, Yongwang Li, Hans Niemantsverdriet, Weichang Hao, Ren Su
Summary: This study utilizes metal cocatalysts to activate alcohols in photocatalytic reactions, separating the stepwise dehydrogenative-condensation process to imine and the direct condensation process to secondary amine. The Rh/TiO2 catalyst promotes the photocatalytic dehydrogenation of alcohol into aldehyde, allowing rapid condensation with aniline to yield imine. On the other hand, Fe/TiO2 catalyst activates the alcohol mildly and enables direct dehydrative coupling with aniline to produce secondary amine. Both Rh/TiO2 and Fe/TiO2 photocatalysts show excellent performance in terms of conversion, selectivity, stability, and a wide substrate scope, making this strategy promising for applications.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2022)
Article
Chemistry, Multidisciplinary
Jiajia Li, Junmin Chen, Hefeng Zhu, Mingzhong Cai
Summary: A new mesoporous SBA-15-anchored triphenylphosphine-gold(i) complex [SBA-15-Ph(3)PauNTf(2)] was synthesized and characterized. This catalyst allowed for the photosensitizer-free cross-coupling reaction of aryldiazonium tetrafluoroborates and alkynyltrimethylsilanes under blue LED irradiation, yielding diverse arylalkynes with good yields and high functional group tolerance. The catalyst could be easily recovered and reused multiple times without significant loss in activity.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Cheng-Hsin Ou Yang, Wan-Hsuan Liu, Sheng Yang, Yao-Yu Chiang, Jiun-Jie Shie
Summary: In this paper, a simple protocol for the synthesis of (E)-β-aminoacrylonitriles via Cu(OAc)(2)-mediated nucleophilic addition and oxidation reactions is described. The method shows high effectiveness and stereoselectivity with various substrates. The reactions proceed under mild conditions without the need for additional additives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chao-Jiu Long, Hong-Ping Pu, Ya-Nan Zhao, Yan-Hong He, Zhi Guan
Summary: Researchers developed a new enantioselective oxidative cross-dehydrogenative coupling method by combining photocatalysis and l-/d-proline catalysis. Acyclic benzylic secondary amines were successfully transformed into beta-amino carbonyl compounds with good yields up to 86% and high enantio- and diastereoselectivities (up to 99% ee and > 99 : 1 dr) under mild and oxidant-free conditions. This method has wide substrate scope, excellent functional group tolerance, and simple operation.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Mohd. Zaheeruddin Beg, Pravin K. Singh, Praveen P. Singh, Manish Srivastava, Vishal Srivastava
Summary: An efficient visible light-mediated, eosin Y-catalyzed direct C-H oxidative amination reaction of benzoxazoles with secondary amines has been developed, providing a straightforward, green, and environmentally friendly approach to a wide variety of substituted benzoxazole-2-amines under mild reaction conditions. Biological studies such as drug-likeness and molecular docking have also been conducted on the molecule.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Organic
August Runemark, Henrik Sunden
Summary: An additive-free, visible light-driven annulation between N-aryl amino acids and maleimide to form tetrahydroquinolines (THQs) is reported, where the photochemical activation of an electron donor-acceptor (EDA) complex drives the reaction. Aerobic oxygen acts as the terminal oxidant in the net oxidative process. Various N-aryl amino acids and maleimides have been investigated as substrates, leading to good to excellent yields of the target THQ. Mechanistic investigations using titration and UV-vis studies confirm the crucial role of the EDA complex as the photoactive species.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Alexey L. Kaledin, Jose B. Roque, Richmond Sarpong, Djamaladdin G. Musaev
Summary: The study demonstrates a feasible Cu(I)-mediated deconstructive fluorination mechanism for N-benzoylated cyclic amines with Selectfluor (R) through calculations, providing a theoretical basis for the reaction.
TOPICS IN CATALYSIS
(2022)
Review
Biochemistry & Molecular Biology
Amarendra Mohan Khan, Narinder Kumar Agnihotri, Vinay Kumar Singh, Subash Chandra Mohapatra, Divya Mathur, Manish Kumar, Rajesh Kumar
Summary: Biocatalysts have emerged as a sustainable alternative to conventional synthetic catalysts, exhibiting excellent selectivity and tolerance in the transformations of nucleosides and their analogs, particularly due to their multiple chiral centers.
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
(2021)
Article
Chemistry, Medicinal
Koen Vandyck, Geert Rombouts, Bart Stoops, Abdellah Tahri, Ann Vos, Wim Verschueren, Yiming Wu, Jingmei Yang, Fuliang Hou, Bing Huang, Karen Vergauwen, Pascale Dehertogh, Jan Martin Berke, Pierre Raboisson
JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Helene Beucher, Estibaliz Merino, Alexandre Genoux, Thomas Fox, Cristina Nevado
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Jonas Verhoeven, Freija De Vleeschouwer, Hanchu Kong, Kristof Van Hecke, Vineet Pande, Weimei Sun, Ann Vos, Tongfei Wu, Lieven Meerpoel, Jan Willem Thuring, Guido Verniest
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Medicinal
Aldo Peschiulli, Daniel Oehlrich, Frederik Rombouts, Ann Vos, Harrie J. M. Gijsen
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Physical
Helene Beucher, Sudhir Kumar, Estibaliz Merino, Wei-Hsu Hu, Gerrit Stemmler, Sergio Cuesta-Galisteo, Jorge A. Gonzalez, Jakub Jagielski, Chih-Jen Shih, Cristina Nevado
CHEMISTRY OF MATERIALS
(2020)
Article
Chemistry, Medicinal
Sandrine Vendeville, Abdellah Tahri, Lili Hu, Samuel Demin, Ludwig Cooymans, Ann Vos, Leen Kwanten, Joke Van den Berg, Michael B. Battles, Jason S. McLellan, Anil Koul, Pierre Raboisson, Dirk Roymans, Tim H. M. Jonckers
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Helene Beucher, Sudhir Kumar, Roopender Kumar, Estibaliz Merino, Wei-Hsu Hu, Gerrit Stemmler, Sergio Cuesta-Galisteo, Jorge A. Gonzalez, Leonard Bezinge, Jakub Jagielski, Chih-Jen Shih, Cristina Nevado
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Medicinal
Vineet Pande, Weimei Sun, Lijs Beke, Didier Berthelot, Dirk Brehmer, David Brown, Jordi Corbera, Steve Irving, Lieven Meerpoel, Thomas Nys, Marc Parade, Colin Robinson, Cois Sommen, Marcel Viellevoye, Tongfei Wu, Jan Willem Thuring
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Medicinal
Frederik J. R. Rombouts, Ken-ichi Kusakabe, Richard Alexander, Nigel Austin, Herman Borghys, Michel De Cleyn, Deborah Dhuyvetter, Harrie J. M. Gijsen, Brian Hrupka, Tom Jacobs, Soufyan Jerhaoui, Lieve Lammens, Laurent Leclercq, Koichi Tsubone, Tatsuhiko Ueno, Kenji Morimoto, Shunsuke Einaru, Hirokazu Sumiyoshi, An Van den Bergh, Ann Vos, Michel Surkyn, Ard Teisman, Diederik Moechars
Summary: A novel class of BACE1 inhibitors with optimized structure and properties was developed in this study, achieving target selectivity and efficacy. By addressing potential toxicity issues through compound optimization, a drug candidate with potential clinical value was obtained.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Sylvain Oudeyer, Vincent Levacher, Helene Beucher, Jean-Francois Briere
Summary: Recently, there have been significant advancements in radical chemistry in the field of organic synthesis. The use of modern catalytic and technology-driven strategies has allowed for the implementation of highly reactive radical species, expanding the scope of synthetic methodologies. This literature review focuses on the recent progress in radical-based transformations of N,N-disubstituted iminium substrates and the chemistry of N+-X-(X = O, NR) azaarenium dipoles, which have proven to be versatile platforms in this research field. The specific reactivity profiles of N-alkylazaarenium salts in radical chemistry are also discussed.
Article
Chemistry, Multidisciplinary
Pierre Milbeo, Arthur Lebrene, Mariia Savchuk, Giang Vo-Thanh, Sylvain Oudeyer, Helene Beucher, Jean-Francois Briere
Summary: A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes, showcasing an unprecedented sulfa-1,6-conjugate addition and a diastereoselective aldol reaction leading to a formal (4+2) cycloaddition. This research provides a new approach to synthesize bio-relevant and original tricyclic thiochroman derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Helene Beucher, Johannes Schoergenhumer, Estibaliz Merino, Cristina Nevado
Summary: A chelation-assisted oxidative addition of gold(I) into the C-C bond of biphenylene was achieved in this study. The presence of coordinating groups played a crucial role in the successful activation of strained C-C bonds by gold. This research provides a new and straightforward method for synthesizing cyclometalated gold(III) complexes.
Article
Materials Science, Multidisciplinary
Guillaume Bretel, Erwan Le Grognec, Denis Jacquemin, Takashi Hirose, Kenji Matsuda, Francois-Xavier Felpin
ACS APPLIED POLYMER MATERIALS
(2019)
