Article
Chemistry, Physical
Connor S. MacNeil, Hongyu Zhong, Tyler P. Pabst, Michael Shevlin, Paul J. Chirik
Summary: The cobalt-catalyzed asymmetric hydrogenation of dehydro-sitagliptin was studied and applied to the synthesis of sitagliptin. The discovery of catalysts was accelerated by the synthesis of cationic bis(phosphine) cobalt eta 6-arene complexes. The optimal catalyst showed high yield and enantioselectivity, and maintained excellent activity and selectivity after standing in air for 2 weeks.
Article
Chemistry, Organic
Huaxin Yang, Yang Zhou, Zhihan Zhang, Jialin Wen, Xumu Zhang
Summary: We report a convenient method for converting olefins to organic iodides and amines using a specific catalyst, molecular hydrogen, and an electrophilic iodine reagent. High yields and regioselectivities were achieved under mild conditions, and C-N products were obtained through specific workup steps. Control experiments and DFT calculations were conducted to exclude potential reaction pathways.
Article
Chemistry, Multidisciplinary
Yuki Saito, Shu Kobayashi
Summary: The application of heterogeneous catalysts in continuous-flow enantioselective hydroacylation reactions was studied. Catalysts were prepared by mixing supports and rhodium complexes, and showed excellent activity and enantioselectivity. Under optimized conditions, the catalysts exhibited high turnover numbers and could be applied to various substrates. Furthermore, sequential-flow reactions with other heterogeneous catalysts were demonstrated for the synthesis of biologically active molecules and functional materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Nora Jannsen, Cornelia Pribbenow, Carmen Selle, Hans-Joachim Drexler, Marc-Andre Mueller, Jonathan A. Medlock, Werner Bonrath, Detlef Heller
Summary: An efficient and highly selective semi-hydrogenation of terminal alkynes to alkenes has been achieved using neutral dimeric rhodium(I) complexes. The results show excellent selectivity and no deactivation or reduction in selectivity, indicating the potential industrial application of homogeneous rhodium complexes in the semi-hydrogenation of terminal alkynes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Nora Jannsen, Cornelia Pribbenow, Carmen Selle, Ralf Jackstell, Hans-Joachim Drexler, Marc-Andre Muller, Jonathan A. Medlock, Werner Bonrath, Detlef Heller
Summary: The study successfully achieved the selective reduction of terminal alkynes to alkenes using specific rhodium catalysts. Although catalyst deactivation occurs at high concentrations, several strategies were proposed to overcome this deactivation.
Article
Chemistry, Multidisciplinary
Jie Gao, Rui Ma, Lu Feng, Yuefeng Liu, Ralf Jackstell, Rajenahally V. Jagadeesh, Matthias Beller
Summary: This study introduces a general protocol for the selective hydrogenation and deuteration of alkenes, utilizing a specific nickel-graphitic shell-based core-shell-structured catalyst to achieve high yields of corresponding alkanes and deuterium-labeled alkanes at ambient conditions. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated through gram-scale reactions and efficient catalyst recycling experiments.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Zhenpeng Liu, Lei Zhang, Zhipeng Ren, Jian Zhang
Summary: Selective electrochemical hydrogenation of alkynes to alkenes under ambient conditions is a promising alternative to traditional thermocatalytic hydrogenation methods. This comprehensive review summarizes recent achievements in electrocatalysts including noble metal and non-noble metal materials. Effective catalyst design strategies to improve alkyne conversion and alkene selectivity, such as accelerating active hydrogen species formation and suppressing side reactions, are highlighted. In addition, the advantages and disadvantages of various electrolyzers are systematically discussed. Major challenges and future trends in this field are proposed.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Wen-Jie Kang, Bo Li, Meng Duan, Guangxing Pan, Weiqiang Sun, Aishun Ding, Yanbin Zhang, K. N. Houk, Hao Guo
Summary: The study found that using TfOH as a co-catalyst can tune the properties of TX to make it a photoredox catalyst with highly enhanced oxidative capability, successfully applied in the hydrogenation of alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Antonio Del Vecchio, Harry R. Smallman, Jennifer Morvan, Tom McBride, Duncan L. Browne, Marc Mauduit
Summary: This article introduces the versatility of olefin metathesis and its successful applications in natural product synthesis and the valorization of renewable feedstocks. In addition, flow chemistry has gained significant interest as a valuable alternative to traditional batch chemistry and has paved the way for new transformations. The article highlights the promising application of continuous-flow methods in olefin metathesis, addressing typical issues such as undesired self-reactions and ethylene-mediated catalyst deactivation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Edward Masson, Erin M. Maciejewski, Katherine M. P. Wheelhouse, Lee J. Edwards
Summary: Fixed bed reactors (FBR) have been widely used in the petrochemical/fine chemical industries since the 1930s, but only in the last two decades have they started to be utilized in the pharmaceutical industry. While most engineering knowledge is transferable, there are unique challenges in the pharmaceutical industry, such as reactor scale and catalyst requirements. However, there have been relatively few reported processes scaled within the pharmaceutical industry.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Multidisciplinary
Yuki Saito, Ken Nishizawa, Benjamin Laroche, Haruro Ishitani, Shu Kobayashi
Summary: This study demonstrates the continuous-flow synthesis of (R)-tamsulosin without the need for the isolation or purification of any intermediates or byproducts. The synthesis was achieved through four catalytic transformations in a flow stream, resulting in a high yield and enantiomeric excess.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Suguru Murakami, Ryosuke Matsubara, Masahiko Hayashi
Summary: In this study, the reaction between alkynes and bis(pinacolato)diboron in the presence of [Cp*RuCl2](n) was successfully applied to synthesize (Z)-1,2-diboryl alkenes. The addition of NaOC6H4(4-tBu) and methanol in proper amounts was crucial for achieving high product yield. The obtained 1,2-diboryl alkenes served as precursors for tetrasubstituted alkenes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alexia N. Kim, Aurapat Ngamnithiporn, Michael D. Bartberger, Brian M. Stoltz
Summary: The first asymmetric trans-selective hydrogenation of 1,3-disubstituted isoquinolines has been developed, resulting in enantioenriched trans-tetrahydroisoquinolines in good yield with high enantioselectivity. Mechanistic studies reveal the crucial role of non-coordinating chlorinated solvents and halide additives in enabling trans-selectivity.
Article
Chemistry, Physical
Tanuja Tewari, Rohit Kumar, Samir H. Chikkali
Summary: An iron-catalyzed, magnesium-mediated, formal hydroformylation method for alkynes and alkenes in the absence of syngas has been reported. The reaction proceeds with good to excellent conversion and selectively produces alpha,beta-unsaturated aldehydes. Mechanistic investigations revealed the presence of vinyl magnesium intermediate, and the control experiment confirmed the iron catalyst's homogeneous nature.
Article
Chemistry, Physical
Bingxue Liu, Qiang Liu
Summary: Cobalt-catalyzed hydroalkylation of alkenes and alkynes is an efficient method for selective formation of C-C bonds. Significant progress has been made in the past five years, covering different reaction mechanisms.
Article
Chemistry, Multidisciplinary
Aske S. Donslund, Simon S. Pedersen, Cecilie Gaardbo, Karoline T. Neumann, Lee Kingston, Charles S. Elmore, Troels Skrydstrup
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Multidisciplinary Sciences
Per Plenge, Ara M. Abramyan, Gunnar Sorensen, Arne Mork, Pia Weikop, Ulrik Gether, Benny Bang-Andersen, Lei Shi, Claus J. Loland
NATURE COMMUNICATIONS
(2020)
Correction
Radiology, Nuclear Medicine & Medical Imaging
N. Stergiou, E. T. Wunsche, I. Mes, M. Schreurs, M. Verlaan, E. J. M. Kooijman, A. D. Windhorst, G. A. M. S. Dongen, L. Helboe, S. Vergo, S. Christensen, A. Asuni, A. Jensen, B. Bang-Andersen, D. J. Vugts, W. Beaino
NUCLEAR MEDICINE AND BIOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Stephanie J. Ton, Karoline T. Neumann, Peter Norby, Troels Skrydstrup
Summary: This paper presents a direct synthetic route for full carbon isotope replacement of aliphatic carboxylates via nickel-mediated alkoxycarbonylation, allowing for carbon-13 labeling of several pharmaceutically active compounds. Mechanistic investigations suggest an alternative pathway for carboxylation, involving attack of an open shell species generated from the alkyl halide. The methodology provides a simple and convenient setup for synthesis and carbon isotope labeling while offering new insights on the reactivity of the N2N nickel pincer complex.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Pharmacology & Pharmacy
Andrea Varrone, Christoffer Bundgaard, Benny Bang-Andersen
Summary: In central nervous system drug discovery, PET is a crucial tool for assessing the distribution and binding of new chemical entities in the brain. This review summarizes the main applications of PET in early drug development and proposes aligned nomenclatures for key pharmacokinetic parameters to guide PET studies.
CLINICAL PHARMACOLOGY & THERAPEUTICS
(2022)
Article
Neurosciences
Lone Helboe, Nina Rosenqvist, Christiane Volbracht, Lars O. Pedersen, Jan T. Pedersen, Soren Christensen, Jan Egebjerg, Claus T. Christoffersen, Benny Bang-Andersen, Thomas G. Beach, Geidy E. Serrano, Jeppe Falsig
Summary: This study investigated the heterogeneity of tau pathology across different tauopathies and evaluated the binding properties of the humanized pS396-tau antibody hC10.2 and other anti-tau antibodies. The findings showed that hC10.2 is a promising therapeutic tau antibody for the treatment of AD and primary tauopathies.
JOURNAL OF ALZHEIMERS DISEASE
(2022)
Article
Biochemistry & Molecular Biology
Jens D. Mikkelsen, Sanjay S. Aripaka, Sif Kaad, Burcu A. Pazarlar, Lars Pinborg, Bente Finsen, Andrea Varrone, Benny Bang-Andersen, Jesper F. Bastlund
Summary: A newly developed radioligand [JNJ-64413739] that selectively binds to the purinergic receptor P2X7R has been found to detect neuroinflammation in the brain. The binding properties of JNJ-64413739 in human brain tissue were investigated, and it was found to have different binding abilities in gray and white matter. These findings demonstrate that JNJ-64413739 is suitable for evaluating the distribution and expression of P2X7R in the human brain.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Radiology, Nuclear Medicine & Medical Imaging
N. Stergiou, T. E. Wuensche, M. Schreurs, I. Mes, M. Verlaan, E. J. M. Kooijman, A. D. Windhorst, L. Helboe, S. Vergo, S. Christensen, A. A. Asuni, A. Jensen, G. A. M. S. Van Dongen, B. Bang-Andersen, D. J. Vugts, W. Beaino
Summary: This study used Zr-89-immuno-PET to evaluate the targeting and distribution of a bispecific brain-shuttle IgG, Adu-8D3, as a potential theranostic for AD. The results showed high specific uptake of Adu-8D3 in the brain, indicating its potential for early detection of A beta plaque pathology.
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2023)
News Item
Chemistry, Multidisciplinary
Karoline T. Neumann, Troels Skrydstrup
Summary: The direct carbon isotope exchange reaction on alpha-amino acids is highly desirable as it allows for the direct formation of C-11, C-13, and C-14-labelled alpha-amino acids. This new method involving aldehyde-catalysed carboxylate exchange with isotopically labelled *CO2 bypasses the need for multiple synthetic steps and harsh conditions.
Article
Chemistry, Organic
Nicklas P. Corneliussen, Ebbe K. Grove, Anne-Sofie O. Scholer, Anton H. Andersen, Aske S. Donslund, Karoline T. Neumann, Troels Skrydstrup
Summary: We describe a nickel-catalyzed carbonylative cross-coupling reaction between alkyl zinc reagents and alpha,alpha-difluorobromoacetamides to obtain alpha,alpha-difluoro-beta-ketoamides in moderate to good yields. Unlike previous reports using palladium catalysts, the reaction is catalyzed by a stable nickel(II) pincer complex. The carbonylative reaction occurs in a two-chamber system (COware) where carbon monoxide (CO) is generated ex situ and consumed in the adjacent chamber. The reaction is conducted at low temperatures with near-stoichiometric amounts of CO, allowing for easy access to isotopically labeled products using C-13-labeled SilaCOgen.
Article
Medicine, Research & Experimental
Thomas E. Wuensche, Natascha Stergiou, Iris Mes, Mariska Verlaan, Maxime Schreurs, Esther J. M. Kooijman, Bart Janssen, Albert D. Windhorst, Allan Jensen, Ayodeji A. Asuni, Benny Bang-Andersen, Wissam Beaino, Guus A. M. S. Dongen, Danielle J. Vugts
Summary: This study demonstrated the effectiveness of 89Zr-immuno-PET in imaging and quantifying amyloid-beta specific brain uptake. The use of the novel chelator DFO* showed superior results compared to DFO.
Meeting Abstract
Radiology, Nuclear Medicine & Medical Imaging
Thomas Wuensche, Natascha Stergiou, Iris Mes, Mariska Verlaan, Maxime Schreurs, Esther Kooijman, Bart Janssen, Albert Windhorst, Soren Christensen, Allan Jensen, Ayodeji Asuni, Benny Bang-Andersen, Wissam Beaino, Guus van Dongen, Danielle Vugts
NUCLEAR MEDICINE AND BIOLOGY
(2022)
Meeting Abstract
Radiology, Nuclear Medicine & Medical Imaging
N. Stergiou, T. Wunsche, M. Schreurs, I. Mes, M. Verlaan, E. Kooijman, A. Windhorst, G. van Dongen, L. Helboe, S. Vergo, S. Christensen, A. Asuni, A. Jensen, B. Bang-Andersen, D. Vugts, W. Beaino
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2021)
Meeting Abstract
Radiology, Nuclear Medicine & Medical Imaging
Natascha Stergiou, Thomas Wuensche, Iris Mes, Maxime Schreurs, Mariska Verlaan, Esther Kooijman, Albert Windhorst, Guus van Dongen, Lone Helboe, Sandra Vergo, Soren Christensen, Ayodeji Asuni, Allan Jensen, Benny Bang-Andersen, Danielle Vugts, Wissam Beaino
NUCLEAR MEDICINE AND BIOLOGY
(2021)
Article
Chemistry, Organic
Martin B. Johansen, Anders T. Lindhardt
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)