Magnus Rueping

Magnus Rueping

About

522
Publications
37,651
Reads
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29,861
Citations
Additional affiliations
April 2009 - July 2002
University of Zurich
Position
  • PhD studies
August 2004 - April 2009
Goethe-Universität Frankfurt am Main
Position
  • Professor (Assistant)
July 2002 - August 2004
Harvard University
Position
  • PostDoc Position

Publications

Publications (522)
Article
A decarboxylative cyanation of amino acids under paired electrochemical reaction conditions has been developed. 4-CN-pyridine was found to be a new and effective cyanation reagent under catalyst-free conditions. Mechanistic studies support a nucleophilic reaction pathway, and the cyanation protocol can be applied to diverse substrates including N,N...
Article
Dedicated to NSYSU Chemistry Department's 40th Anniversary. The design incorporates some of NSYSU's distinct features. These are the scenic Sizihwan bay, famous for its beautiful sunset, and the Monkey Mountain, home to the endemic Formosan rock macaques. Starting from the Aza‐o‐QM mountain, different N‐heterocycles were obtained through reactions...
Article
Full-text available
Palladium catalysis induced by visible-light irradiation is a promising tool for promoting unusual chemical transformations. We describe the development of excited-state palladium-catalyzed reductive alkylation of imines with alkyl bromides. The new methodology shows broad functional group tolerance and can additionally be applied in the direct thr...
Article
Herein, we report a reductive cross‐coupling reaction of α‐oxy halides, simply generated from aldehydes, with a series of C(sp2)‐ and C(sp)‐electrophiles. A wide range of aryl and heteroatom aryl halides, vinyl bromides, alkynyl bromides, and acyl chlorides react with unhindered and hindered aldehyde‐derived α‐oxy halides by providing protected alc...
Article
Herein, we report a reductive cross‐coupling reaction of α‐oxy halides, simply generated from aldehydes, with a series of C(sp2)‐ and C(sp)‐electrophiles. A wide range of aryl and heteroatom aryl halides, vinyl bromides, alkynyl bromides, and acyl chlorides react with unhindered and hindered aldehyde‐derived α‐oxy halides by providing protected alc...
Article
Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nano...
Article
Full-text available
Trisubstituted alkenes are important organic synthons and have broad applications in the synthesis of many pharmaceuticals and materials. The stereoselective synthesis of such compounds has long been a research focus for organic researchers. Herein, we report a three-component, reductive cascade, cross-coupling reaction for the arylalkylation of al...
Article
The aza‐ ortho ‐quinone methide (aza‐ o ‐QM) chemistry has overwhelmingly progressed in the past few decades. This review aims to integrate various transition metal‐catalyzed and organocatalytic strategies in taming aza ‐o‐ QM intermediates, including its the aza‐ para ‐quinone methide (aza‐ p ‐QM), aza‐ ortho ‐vinylidene quinone methide (aza‐ o ‐V...
Article
Full-text available
Three-dimensional (3D) bioprinting has emerged as a promising method for the engineering of tissues and organs. Still, it faces challenges in its widespread use due to issues with the development of bioink materials and the nutrient diffusion barrier inherent to these scaffold materials. Herein, we introduce a method to promote oxygen diffusion thr...
Article
A nickel‐catalyzed three‐component reductive carbonylation of alkyl halides, aryl halides, and ethyl chloroformate is described. Ethyl chloroformate is utilized as a safe and readily available source of CO in this multi‐component protocol, providing an efficient and practical alternative for the synthesis of aryl‐alkyl ketones. The reaction exhibit...
Article
A nickel‐catalyzed three‐component reductive carbonylation of alkyl halides, aryl halides, and ethyl chloroformate is described. Ethyl chloroformate is utilized as a safe and readily available source of CO in this multi‐component protocol, providing an efficient and practical alternative for the synthesis of aryl‐alkyl ketones. The reaction exhibit...
Article
Full-text available
Various methods that use a photocatalyst for electron transfer between an organic substrate and a transition metal catalyst have been established. While triplet sensitization of organic substrates via energy transfer from photocatalysts has been demonstrated, the sensitization of transition metal catalysts is still in its infancy. Here, we describe...
Article
Full-text available
Hydride transfers are key to a number of economically and environmentally important reactions, including H2 evolution and NADH regeneration. The electrochemical generation of hydrides can therefore drive the electrification of chemical reactions to improve their sustainability for a green economy. Catalysts containing molybdenum have recently been...
Article
Full-text available
The addition of a B-H bond to an unsaturated bond (polarized or unpolarized) is a powerful and atom-economic tool for the synthesis of organoboranes. In recent years, s-block organometallics have appeared as alternative catalysts to transition-metal complexes, which traditionally catalyze the hydroboration of unsaturated bonds. Because of the recen...
Article
Full-text available
In the biosynthesis sterols an enzyme-catalyzed demethylation is achieved via a stepwise oxidative transformation of alcohols to olefins. The overall demethylation proceeds through two sequential monooxygenation reactions and a subsequent dehydroformylative saturation. To mimic the desaturation processes observed in nature, we have successfully int...
Article
Divergent synthesis of medium-sized rings with controllable ring sizes represents a longstanding challenge in organic synthesis. Herein, we developed a transition-metal-catalyzed switchable divergent cycloaddition of para-quinone methides and vinylethylene carbonates by controlling the steric hindrance of substituent. Different from reported alkoxi...
Article
A metal-free synthesis of enantiopure β-substituted tryptophan derivatives was developed. A chiral Brønsted acid enabled the addition of donor-substituted hydrazones to 3-indolylmethanols in excellent yields and enantioselectivities.
Article
Metal-free C-Se cross-couplings via the formation of electron-donor-acceptor (EDA) complexes have been developed. The visible-light induced reactions can be applied for the synthesis of a series of unsymmetrical diaryl selenides...
Article
Metallaphoto-catalysis has been established as a robust platform for efficient construction of a range of chemical bonds. Moreover, transformation of native functionalities such as C(sp3)-H bonds to produce functional molecules represents one of the most attractive strategies in organic synthesis. Merging two powerful methodologies, metallaphoto-ca...
Article
Conventionally, the virtue of porosity is only given to porous solids. Metal Organic Frameworks (MOFs), carbon materials, or zeolites are some examples. However, processing these solids is not a straightforward task. Here, we discuss how to endow porous solids (MOFs) with liquid phase processability. More specifically, we show that surface modifica...
Article
Full-text available
The Red Sea is a marine environment with unique chemical characteristics and physical topographies. Among the various habitats offered by the Red Sea, the deep-sea brine pools are the most extreme in terms of salinity, temperature and metal contents. Nonetheless, the brine pools host rich polyextremophilic bacterial and archaeal communities. These...
Article
The catalytic enantioselective oxidative hetero-coupling of arenols using a chiral vanadium(v) complex has been developed. The coupling of hydroxycarbazole derivatives with various arenols provided axially chiral biarenols with high chemo-, regio-, and enantioselectivities. The reaction took place under mild conditions and exhibited satisfactory fu...
Article
Profound pharmacological benefits can be provided by site‐selective incorporation of the deuterated “magic methyl” group, which can be considered an important tool for drug optimization and development. This review highlights site‐selective trideuteromethylation strategies according to the trideuteromethylation reagent used and describes the mechan...
Article
Full-text available
A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonami...
Article
Full-text available
In the field of medicinal chemistry the precise installation of a trideuteromethyl group is gaining ever‐increasing attention. Site‐selective incorporation of the deuterated “magic methyl” group can provide profound pharmacological benefits and can be considered as an important tool for drug optimization and development. This review provides a stru...
Article
The addition of a Y-H (Y= B, Si, Sn, N, P and O) bonds and H2 to unsaturated bonds is a powerful and atom economic method for the synthesis of fine chemicals. In the recent years, magnesium-based organometallic complexes have appeared as an alternative to transition metal catalysts for the hydrofunctionalization and hydrogenation of unsaturated sys...
Article
A highly regioselective protocol for the synthesis of isoxazolines through cascade C−O and C−Br bond formation has been developed. The electrochemical approach uses traceless electrons as a sole source of oxidant, thus avoiding the use of stoichiometric organic or inorganic oxidants and provides a mild and environmentally benign alternative pathway...
Article
Full-text available
The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, afford...
Article
Full-text available
Extremophiles are remarkable organisms that thrive in the harshest environments on Earth, such as hydrothermal vents, hypersaline lakes and pools, alkaline soda lakes, deserts, cold oceans, and volcanic areas. These organisms have developed several strategies to overcome environmental stress and nutrient limitations. Thus, they are among the best m...
Article
Full-text available
The haloarchaeon Halorubrum lacusprofundi is among the few polyextremophilic organisms capable of surviving in one of the most extreme aquatic environments on Earth, the Deep Lake of Antarctica (−18 • C to +11.5 • C and 21-28%, w/v salt content). Hence, H. lacusprofundi has been proposed as a model for biotechnology and astrobiology to investigate...
Article
Full-text available
The biotin–streptavidin interaction is among the strongest known in nature. Herein, the site-directed incorporation of biotin and 2-iminobiotin composed of noncanonical amino acids (ncAAs) into proteins is reported. 2-Iminobiotin lysine was employed for protein purification based on the pH-depen- dent dissociation constant to streptavidin. By using...
Article
Full-text available
the pyrrolysyl-tRnA synthetase (pylRS) and its cognate tRnA pyl are extensively used to add non-canonical amino acids (ncAAs) to the genetic code of bacterial and eukaryotic cells. However, new ncAAs often require a cumbersome de novo engineering process to generate an appropriate pylRS/ tRnA pyl pair. We here report a strategy to predict a PylRS v...
Article
Full-text available
Enzymes originating from hostile environments offer exceptional stability under industrial conditions and are therefore highly in demand. Using sin- gle-cell genome data, we identified the alcohol dehydrogenase (ADH) gene, adh/a1a, from the Atlantis II Deep Red Sea brine pool. ADH/A1a is highly active at elevated temperatures and high salt concentr...
Article
Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol.% loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart‐Wallach (NH4CO2H) type reaction as...
Patent
The present disclosure describes materials and methods for providing a solution- processable metal-organic framework (MOF) powder, and dispersions containing the same, including Mixed Matrix Membranes. A solution-processable metal- organic framework (MOF) powder comprising a MOF nanoparticle having a dispersion-stabilizing moiety bonded to a metal...
Article
Herein we report the deoxygenated fluorination of readily available carboxylic acids. A series of acyl fluorides have been synthesized using shelf-stable N-trifluoromethylthiophthalimide as a fluorinated reagent for the first time....
Article
Full-text available
The combination of well-defined molecular cavities and chemical functionality makes crystalline porous solids attractive for a great number of technological applications, from catalysis to gas separation. However, in contrast to other widely applied synthetic solids such as polymers, the lack of processability of crystalline extended solids hampers...
Article
The formation of C‐heteroatom bonds represents an important type of bond‐forming reaction in organic synthesis and often provides a fast and efficient access to privileged structures found in pharmaceuticals, agrochemical and materials. In contrast to conventional Pd‐ or Cu‐catalyzed C‐heteroatom cross‐couplings under high‐temperature conditions, r...
Article
The generation of NiIII and excited NiII intermediates facilitates the reductive elimination step leading to the mild cross‐couplings. This review provides an overview of the state‐of‐the‐art approaches for mild C‐heteroatom bond formations via homo‐ and heterogeneous photoredox and nickel dual catalysis, electro‐ and nickel dual catalysis, as well...
Article
Full-text available
The haloarchaeon Halorubrum lacusprofundi is among the few polyextremophilic organisms capable of surviving in one of the most extreme aquatic environments on Earth, the Deep Lake of Antarctica (−18 °C to +11.5 °C and 21–28%, w/v salt content). Hence, H. lacusprofundi has been proposed as a model for biotechnology and astrobiology to investigate po...
Article
We report here a comprehensive computational analysis of the mechanisms of the photoredox-nickel-HAT (HAT: hydrogen atom transfer) catalyzed arylation and alkylation of α-amino Csp3-H bonds developed by MacMillan and coworkers. Different alternatives for the three catalytic cycles were tested to identify unambiguously the operative reaction mechani...
Article
The first base metal-catalyzed transfer hydrogenation of alkynes with methanol is described. An air and moisture stable manganese pincer complex catalyzes the reduction of a variety of different alkynes to the corresponding (Z)-olefins in high yields. The reaction is stereo- and chemoselective and scalable.
Article
Full-text available
An unexpected magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epox-ides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mecha-nistic investigations and DFT calculatio...
Article
A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifun...
Article
An unprecedented base metal catalysed asymmetric synthesis of α-chiral amine precursors from racemic alcohols is reported. This redox-neutral reaction utilises a bench-stable manganese complex and Ellman’s sulfinamide as versatile ammonia...
Article
As shown in article number 1902115, Srinivas Banala and co‐workers have developed PyBODIPYs as a novel class of near‐infrared quenchers for photoacoustic imaging (PAI). The pyrrole conjugation redshifts the absorption maxima, quenches the fluorescence emission completely and exhibits a strong PAI signal due to an intramolecular photoinduced electro...
Article
The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air- and moisture-stable manganese catalyst provides access to either C3- or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes pl...
Article
A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles...
Article
Full-text available
A new catalytic method for the direct alkylation of allylic C(sp ³ )–H bonds from unactivated alkenes via synergistic organo- and photoredox catalysis is described.
Preprint
Full-text available
There were warnings before; nevertheless the current CoVID-19 pandemic took the world by surprise: within just four month, it conquered the globe and claimed over 200'000 lives. Unprecedented governmental actions put about half of the population under curfew or lock-down. The resulting economic meltdown is expected to eliminate globally 9'000'000'0...
Article
Full-text available
Environments previously thought to be uninhabitable offer a tremendous wealth of unexplored microorganisms and enzymes. In this paper, we present the discovery and characterization of a novel γ-carbonic anhydrase (γ-CA) from the polyextreme Red Sea brine pool Discovery Deep (2141 m depth, 44.8 • C, 26.2% salt) by single-cell genome sequencing. The...
Article
Full-text available
Photoacoustic imaging (PAI) is a rapidly evolving field in molecular imaging that enables imaging in the depths of ultrasound and with the sensitivity of optical modalities. PAI bases on the photoexcitation of a chromophore, which converts the absorbed light into thermal energy, causing an acoustic pressure wave that can be captured with ultrasound...
Article
We report a dual catalytic system for the direct benzylic C-H acylation reaction furnishing a variety of unsymmetrical ketones. A benzophenone-derived photosensitizer combined with a nickel catalyst has been established...
Article
A new catalytic enantioselective hydroarylation of unactivated olefins is developed that provides rapid access to functionalized chiral dihydrobenzofurans with good yields and excellent enantioselectivities. Simple aromatic ketones or amides act as a directing group allowing the regioselective reaction at the more hindered ortho position. Tertiary...
Article
Full-text available
Cascade reactions that produce multiple chemical bonds in one synthetic operation are important in the efficient construction of complex molecules. In addition, photoredox and nickel dual catalysis opens a new and powerful avenue for transition-metal-catalyzed cross-coupling reactions. By combining these two concepts, photoredox and nickel dual-cat...
Article
Full-text available
Photoacoustic imaging (PAI) is increasingly employed in (pre‐) clinical research, thus, development of suitable contrast agents, in particular fluorescence‐quenched chromophores, for PAI is of high importance. Small molecule dyes are appropriate due to favorable circulation, excretion properties, and ease of conjugation to targeting moieties. The B...
Article
Full-text available
Environments previously thought to be uninhabitable offer a tremendous wealth of unexplored microorganisms and enzymes. In this paper, we present the discovery and characterization of a novel γ-carbonic anhydrase (γ-CA) from the polyextreme Red Sea brine pool Discovery Deep (2141 m depth, 44.8°C, 26.2% salt) by single-cell genome sequencing. The ex...
Article
The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as alcohols...