catalysis, electrochemistry, peptides, computation, late-stage diversification, in 3d
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Articles by Lutz Ackermann
Modular Access to α -Tertiary Amines: Electrochemical Tandem Di-Functionalization of Olefins With Ammonia Surrogates and Amino Acids
1 Introduction The presence of quaternary carbon centers in small molecules allows for restricted conformation and three-dimensional structure, which are highly desirable for applications in drug discovery [1-5]. Further, construction of quaternary carbon centers remains challenging primarily due to the large steric factor, and, often, the presence of a nitrogen substituent consequently limits the approaches developed so far in this direction [6, 7].
Enantio- and regioselective nickel/photoredox-catalyzed cross-electrophile coupling of benzylic aziridines with alkynyl bromides
Abstract Alkynes with a proximal stereogenic center are a key structural element of many bioactive compounds, chemical probes, and functional materials and serve as a valuable synthon in organic synthesis.
Single-pot mechanochemically-enabled fluorine atom closed-loop economy using PFASs as fluorinating agents
Abstract Per- and polyfluoroalkyl substances (PFASs), also known as “forever chemicals”, pose an increasing threat to the environment and human health. Despite recent advancements in PFASs destruction, the recycling processes for such molecules remain limited to methods using high-temperatures or strong reducing agents. Sustainable degradation methods for PFASs, along with the subsequent utilization or recycling of the resulting fluorides, are indeed highly beneficial.
Mechanochemical ligand-controlled regiodivergent hydroarylation of alkenes via iron-catalyzed C−H activation - Nature Communications
Abstract The iron-catalyzed hydroarylation of alkenes with indoles is a sustainable, effective synthetic transformation towards the construction of functionalized indoles - crucial motifs for various bioactive molecules and drug candidates. However, such transformations have proven challenging for unactivated alkenes, and the requirement for (super)stoichiometric amounts of reactive Grignard reagents has limited broader applications.
Nickelaelectro-Catalyzed Glycosyl-Donor Activation Enabling α-C-Alkenyl Glycoside Assembly
C-glycosides featuring a direct carbon–carbon bond at the anomeric position are prevalent scaffolds in prominent natural products, which present notable medicinal value. (1) Among them, C-alkenyl glycosides form a distinct subclass distinguished by a carbon–carbon double bond at the anomeric position, which replaces the traditional C–O glycosidic linkage.
Nickelaelectro-Catalyzed Glycosyl-Donor Activation Enabling α-C-Alkenyl Glycoside Assembly
C-glycosides featuring a direct carbon–carbon bond at the anomeric position are prevalent scaffolds in prominent natural products, which present notable medicinal value. (1) Among them, C-alkenyl glycosides form a distinct subclass distinguished by a carbon–carbon double bond at the anomeric position, which replaces the traditional C–O glycosidic linkage.
Expedient access to methylamine with potential - Nature Chemistry
Traditional methylamine synthesis from methanol and ammonia relies on high-temperature and high-pressure reaction conditions, resulting in byproducts and challenging purification. Now, electrochemical nitromethane reduction under mild conditions has been realized with a copper catalyst, enabling selective and sustainable methylamine synthesis.
Well-Defined Iron(0) Precatalysts for Grignard-Free C-H Alkenylation at Room Temperature
Introduction Click to copy section linkSection link copied! Transition-metal-catalyzed hydroarylation reactions of alkynes have emerged as a transformative platform for the formation of C–C bonds with full atom economy. (1−5) Despite major progress in this field, such hydroarylations usually rely on precious and rare ruthenium, (6) rhodium, (7) or palladium, (2) as well as toxic transition metals such as cobalt (8) or nickel, (9) thereby significantly limiting their practicability.
A Unified Approach to Meta-Selective Methylation, Mono-, Di- and Trifluoromethylation of Arenes
A Unified Approach to Meta-Selective Methylation, Mono-, Di- and Trifluoromethylation of Arenes Matched molecular series (MMS) are series of molecules that differ only by a single modification at a specific site. The synthesis of MMS is a desirable strategy in drug discovery campaigns. Small aliphatic motifs, notably methyl, mono-, di- and trifluoromethyl substituents (C1 units), are known to have profound effects on the physiochemical properties and/or potency of drug candidates.
Highly‐selective Electrochemical Decarboxylative Late‐Stage Functionalization of Amino Acids
Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Visible Light-Induced Ruthenium(II)-Catalyzed Hydroarylation of Unactivated Olefins
Visible Light-Induced Ruthenium(II)-Catalyzed Hydroarylation of Unactivated Olefins Hydroarylation reactions have emerged as a valuable tool for the direct functionalization of C–H bonds with ideal atom economy. However, common catalytic variants for these transformations largely require harsh reaction conditions, which often translate into reduced selectivites.
Ruthenium(II)-Catalyzed Remote C-H Alkylation of Arenes Using Diverse N-Directing Groups through Aziridine Ring Opening | Organic Letters
Organic Letters Cite this: Org. Lett. 2024, XXXX, XXX Click to copy citationCitation copied! Learn about these metrics Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days. Citations are the number of other articles citing this article, calculated by Crossref and updated daily.
Anodic Commodity Polymer Recycling: The Merger of Iron‐Electrocatalysis with Scalable Hydrogen Evolution Reaction
Introduction Due to their low cost, water resistance, durability, and ease of production, plastics play a key role in a large array of our modern society.1 However, less than 10 % of the world-wide produced plastics are currently recycled, while less than 1 % is recycled more than once.1b, 2 As a direct consequence of this low recycling rate, there is an accumulation of plastic waste in landfills and aquatic environments threatening wildlife, and environment.
Anodic Commodity Polymer Recycling: The Merger of Iron‐Electrocatalysis with Scalable Hydrogen Evolution Reaction
Plastics are omnipresent in our everyday life, and accumulation of post-consumer plastic waste in our environment represents a major societal challenge. Hence, methods for plastic waste recycling are in high demand for a future circular economy. Specifically, the degradation of post-consumer polymers towards value-added small molecules constitutes a sustainable strategy for a carbon circular economy.
Enantioselective Cobaltaphotoredox-Catalyzed C–H Activation
Introduction Click to copy section linkSection link copied! Over the past decades, photochemistry has been identified as an environment-friendly platform for molecular synthesis. (1−9) The merger of photoinduced catalysis with enantioselective catalysis, (10−12) such as organocatalysis, (13−16) enzymatic catalysis, (17) and transition metal catalysis, (18,19) provides a powerful strategy to satisfy the growing demand for enantiomerically pure small molecules.
Traurige Chronik eines wichtigen Abkommens
Stand: 30.05.2013 10:38 Uhr Seit Jahren steht der Textil-Discounter KiK wegen der Arbeitsbedingungen, unter denen er in Südostasien produzieren lässt, in der Kritik. Jetzt hat KiK gemeinsam mit über 30 weiteren Modketten ein Abkommen für mehr Brandschutz und Gebäudesicherheit in Bangladesch unterschrieben, über das lange verhandelt wurde. Die traurige Chronik eines wichtigen Abkommens. 24.
Gefahr beim Augenlasern: Rendite statt Medizin
Stand: 18.07.2013 10:00 Uhr Bei Familie Weinberger sind auch mittags die Rollläden geschlossen. Und selbst dann trägt Andreas Weinberger noch eine Sonnenbrille. Seine Augen sind extrem lichtempfindlich, nachdem er sich operieren ließ. Er wollte keine Brille mehr und machte einen Termin für ein Beratungsgespräch bei einer Augenlaser-Kette. Von Risiken sei nicht die Rede gewesen. Nun läuft er seit Monaten ständig mit Sonnenbrille rum.
Band Aid 30: Das Richtige wollen, das Falsche tun?
Stand: 03.12.2014 10:25 Uhr Zum 30-jährigen Jubiläum der von Bob Geldorf ins Leben gerufenen Spendenkampagne "Band Aid" wurde der Erfolgssong "Do they know it’s Christmas?" neu eingespielt. Erstmals gibt es auch eine deutsche Version. Verantwortlich dafür zeichnet Geldorf-Freund und "Tote Hosen"-Frontman Campino. Das Thema der Kampagne: Ebola-Hilfe. Der Song belegt in England und Deutschland momentan den ersten Platz der Single-Charts.
Well‐Defined Highly‐Coordinated Copper(III) Iodide and Pincer Tris(trifluoromethyl)copper Complexes
Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Electrocatalytic Formal C(sp2)-H Alkylations via Nickel‐Catalyzed Cross‐Electrophile Coupling with Versatile Arylsulfonium Salts
Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Electrocatalytic Formal C(sp2)-H Alkylations via Nickel‐Catalyzed Cross‐Electrophile Coupling with Versatile Arylsulfonium Salts
Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Electrocatalytic Formal C(sp2)−H Alkylations via Nickel‐Catalyzed Cross‐Electrophile Coupling with Versatile Arylsulfonium Salts
Installing sp3-hybridized carbons onto aromatic scaffolds is one of the reliable strategies to improve the rate of clinical success in drug discovery.1 Indeed, Lovering and co-workers introduced the Fsp3 descriptor for the fraction of sp3-hybridized carbon atoms in one molecule and demonstrated that drug candidates with higher Fsp3 values are more likely to pass clinical trials.1 In this context, C(sp2)−C(sp3) bond-forming reactions have played a crucial role and allowed access to various...
Fluorescent coumarin-alkynes for labeling of amino acids and peptides via manganese(I)-catalyzed C–H alkenylation
Fluorescent coumarin-alkynes for labeling of amino acids and peptides via manganese(i)-catalyzed C–H alkenylation† The late-stage fluorescent labeling of structurally complex peptides bears immense potential for molecular imaging. Herein, we report on a manganese(I)-catalyzed peptide C–H alkenylation under exceedingly mild conditions with natural fluorophores as coumarin- and chromone-derivatives.
Late-stage meta-C–H alkylation of pharmaceuticals to modulate biological properties and expedite molecular optimisation in a single step - Nature Communications
Abstract Catalysed C–H activation has emerged as a transformative platform for molecular synthesis and provides new opportunities in drug discovery by late-stage functionalisation (LSF) of complex molecules. Notably, small aliphatic motifs have gained significant interest in medicinal chemistry for their beneficial properties and applications as sp3-rich functional group bioisosteres.
Photoinduced C-H arylation of 1,3-azoles via copper/photoredox dual catalysis
Photoinduced C–H arylation of 1,3-azoles via copper/photoredox dual catalysis† The visible light-induced C–H arylation of azoles has been accomplished by dual-catalytic system with the aid of an inexpensive ligand-free copper(I)-catalyst in combination with a suitable photoredox catalyst. An organic photoredox catalyst, 10-phenylphenothiazine (PTH), was identified as effective, cost-efficient and environmentally-benign alternative to commonly-used, expensive Ir(III)-based complexes.
Ruthenium(II)‐Catalyzed Late‐Stage Incorporation of N‐Aryl Triazoles and Tetrazoles with Sulfonium Salts via C−H Activation
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description anie202402060-sup-0001-misc_information.pdf9.1 MB Supporting Information
Stereoselective assembly of C-oligosaccharides via modular difunctionalization of glycals - Nature Communications
Abstract C-oligosaccharides are found in natural products and drug molecules. Despite the considerable progress made during the last decades, modular and stereoselective synthesis of C-oligosaccharides continues to be challenging and underdeveloped compared to the synthesis technology of O-oligosaccharides.
Electrochemical Enantioselective C-H Annulation by Achiral Rhodium(III)/Chiral Brønsted Base Domino Catalysis
Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Catal. 2024, 14, XXX RETURN TO ARTICLES ASAPPREVResearch ArticleNEXT Yanjun Li Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany , Jiawei Xu Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany , João C. A.
Air‐Stable Bis‐Cyclometallated Iridium Catalysts for Ortho‐Directed C(sp2)−H Borylation
Introduction Over the last two decades, C−H bond activation has transitioned from an academic curiosity to a practical methodology with applications in drug synthesis.1 Among the diversity of bond-forming reactions possible via C−H activation, C−H borylation has been established as a particularly attractive transformation due to the synthetic versatility of the resulting C−B bond.2 Various rhodium,3 cobalt,4 and ruthenium5 based catalytic systems have been designed.
Special Issue on Electrochemically‐Driven Organic Synthesis
Molecular synthesis has gained considerable momentum through the impetus provided by electrochemically-enabled redox manipulation.1 Organic electrosynthesis and electrocatalysis bear a unique potential to substantially improve molecular chemistry and provide a wide range of innovative transformations. While a first electrochemically-driven organic synthesis dates back to Kolbe's decarboxylative homocoupling in 1848,2 organic electrosynthesis has remained largely underexplored.
Weak-coordination-auxiliary aminocatalysis enables directed [3+2] cyclization for 2-acylindolizines
Weak-coordination-auxiliary aminocatalysis enables directed [3+2] cyclization for 2-acylindolizines The synthesis of 2-acylindolizines, possessing a readily modifiable ketone group, is of significant importance as it provides versatile precursors for the preparation of various indolizines.
Late-stage synthesis of heterobifunctional molecules for PROTAC applications via ruthenium-catalysed C‒H amidation - Nature Communications
Abstract PROteolysis TArgeting Chimeras (PROTACs) are heterobifunctional molecules emerging as a powerful modality in drug discovery, with the potential to address outstanding medical challenges. However, the synthetic feasibility of PROTACs, and the empiric and complex nature of their structure-activity relationships continue to present formidable limitations. As such, modular and reliable approaches to streamline the synthesis of these derivatives are highly desirable.
Interdisciplinary electrosynthesis: general discussion
Article type Discussion First published 02 Oct 2023 Faraday Discuss., 2023, Advance Article L. Ackermann, M. Avanthay, B. Batanero, D. G. Boucher, P. Broersen, E. Carroll, V. Flexer, R. Francke, T. Fuchigami, R. Gerulskis, D. P. Hickey, B. Hockin, A. Kuhn, M. J. Milner, S. D. Minteer, K. Moeller, Z. A. Nguyen, T. Nokami, S. Rasul, N. Shida, E. Sokalu, K. Taniguchi and N.
Electrochemical C7‐Indole Alkenylation via Rhodium Catalysis
In recent decades, transition metal-catalyzed selective C−H bond functionalization has become an indispensable, cutting-edge step- and atom-economical1 approach for the design of highly useful bioactive pharmaceuticals.2 Within this framework, indoles and their substituted derivatives have emerged as one of the most researched classes of organic compounds, given their use as functional building blocks in numerous marketed drugs and molecular materials (Figure 1a).3 As a precursor, indole...
Ruthenium‐Catalyzed Aminocarbonylation with Isocyanates Through Weak Coordinating Groups
Introduction Introducing amide functional groups under mild conditions has growing importance due to the ubiquity of such structures in biologically active molecules such as peptides and proteins.
The crucial role of silver(i)-salts as additives in C-H activation reactions: overall analysis of their versatility and applicability
The crucial role of silver(i)-salts as additives in C–H activation reactions: overall analysis of their versatility and applicability Transition-metal catalyzed C–H activation reactions have been proven to be useful methodologies for the assembly of synthetically meaningful molecules. This approach bears intrinsic peculiarities that are important to be studied and comprehended in order to achieve its best performance.
Palladium-Catalyzed Electrooxidative Double C-H Arylation
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2023, XXXX, XXX Zhipeng Lin Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany , João C. A.
Palladium-Catalyzed Electrooxidative Double C-H Arylation
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2023, XXXX, XXX RETURN TO ARTICLES ASAPPREVArticleNEXT Zhipeng Lin Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany , João C. A.
Radical approach for enantioselective amination - Nature Synthesis
Enantioselective electrocatalysis is emerging as an increasingly versatile tool in organic synthesis. Now, by applying asymmetric Lewis acid catalysis with an elaborated ligand design, radical electrochemical amination is accomplished with full selectivity control.
Photoelectro-Catalyzed Undirected C‒H Trifluoromethylation of Arenes: Catalyst Evaluation and Scope
Photoelectro-Catalyzed Undirected C‒H Trifluoromethylation of Arenes: Catalyst Evaluation and Scope Abstract During the last few years, photoelectrocatalysis has evolved as an increasingly viable tool for molecular synthesis. Despite several recent reports on the undirected C‒H functionalization of arenes, thus far, a detailed comparison of different catalysts is missing.
Ruthenium‐Catalyzed Remote Difunctionalization of Nonactivated Alkenes for Double meta‐C(sp2)−H/C‐6(sp3)−H Functionalization
Introduction The difunctionalization of alkenes represents a powerful and atom-economical approach for increasing molecular complexity.1, 2 In recent years, fluorinated radicals have engaged for alkene difunctionalization as an elegant and versatile strategy that enables the straightforward construction of fluorine-containing compounds (Scheme 1a).3 The introduction of fluorine-containing groups can dramatically improve the solubility, lipophilicity, permeability and metabolic stability of...
Special Collection on Organic Electrocatalysis
Electrochemistry represents an attractive approach to discovering new reactions and overcoming current challenges in organic synthesis.1 In particular, electrocatalysis—a process that integrates electrochemistry and homogenous or heterogeneous catalysis—has the potential to substantially improve the scope of synthetic electrochemistry and provide a wide range of useful transformations.2 Innovative research in the past several years has demonstrated that electrochemistry and electrocatalysis...
Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)
Abstract Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient and atom-economic tools to prepare PAHs under exceedingly mild conditions constitutes a long-term goal. Traditional syntheses of PAHs have largely relied on multistep approaches or the conventional Scholl reaction.
Thieme E-Journals - Synlett
PDF Download Buy Article Permissions and Reprints All articles of this category Transition metal-catalyzed C–H activation has emerged as a powerful strategy for molecular synthesis with unique levels of resource economy. Weak secondary dispersion interactions were found to play an essential role in these transformations in terms of kinetic efficacy and selectivity.
Cobalt-catalyzed radical-mediated carbon-carbon scission via a radical-type migratory insertion
Cobalt-catalyzed radical-mediated carbon-carbon scission via a radical-type migratory insertion Jianbiao Liu, Xiao-Jun Liu, João C. A. Oliveira, Dezhan Chen and Lutz Ackermann Abstract Migratory insertions of alkenes into metal–carbon (M–C) bonds are elementary steps in diverse catalytic processes. In the present work, a radical-type migratory insertion that involves concerted but asynchronous M–C homolysis and radical attack was revealed by computations.
Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes
Graphical Abstract Electrochemical difunctionalization of unactivated alkenes were realized utilizing commercially available organofluorine reagents through scission of C−H/C−Br bonds via 1,2-, and 1,4-migration process, leading to di and mono-fluoroalkyl functionalized ketone compounds with good functional group tolerance. This transformation tolerates a diverse set of migrating groups, involving (hetero)arenes, olefins, and alkynes.
A recyclable stereoauxiliary aminocatalyzed strategy for one-pot synthesis of indolizine-2-carbaldehydes - Communications Chemistry
Abstract Indolizine-carbaldehydes with the easily modifiable carbaldehyde group are important synthetic targets as versatile precursors for distinct indolizines. However, the efficient one-pot construction of trisubstituted indolizine-2-carbaldehydes represents a long-standing challenge.
Enantioselective cobaltaelectro-catalyzed C-H activations enabled by hydrogen evolution
Abstract Despite the significant progress in enantioselective catalysis during the past decades, asymmetric redox transformations typically rely on costly transition metals as catalysts, along with the use of stoichiometric amounts of chemical redox agents. The exploitation of electrocatalysis in molecular synthesis represents a sustainable alternative towards value-added molecules through the hydrogen evolution reaction (HER).
Triazole-enabled, iron-catalysed linear/branched selective C-H alkylations with alkenes
Triazole-enabled, iron-catalysed linear/branched selective C–H alkylations with alkenes† Silvia Cattani, a Andrea Secchi, a Lutz Ackermann b and Gianpiero Cera *a Abstract Iron-catalysed C–H alkylations with alkenes were achieved on benzamides by N-triazole assistance. A notable switch of the regioselectivity from linear to branched was observed depending on the nature of the olefin employed.
Ruthenium(II)/Imidazolidine Carboxylic Acid‐Catalyzed C−H Alkylation for Central and Axial Double Enantio‐Induction
Introduction In recent years, ruthenium(II)-catalyzed C−H activation has emerged as an increasingly-powerful strategy for efficient molecular synthesis.1, 2 Thus, seminal contributions on ruthenium(II)-catalyzed C−H transformations by Oi and Inoue,2f Ackermann,2d as well as Bruneau and Dixneuf,1a demonstrated its distinct reactivity and selectivity.
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