Featured
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Article |
Host immunomodulatory lipids created by symbionts from dietary amino acids
The symbiotic gut bacterium Bacteroides fragilis produces unique α-galactosylceramides from host dietary branched-chain amino acids, which are presented as CD1d ligands and immunomodulate natural killer T cells.
- Sungwhan F. Oh
- , T. Praveena
- & Dennis L. Kasper
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Article |
A synthetic antibiotic class overcoming bacterial multidrug resistance
Structure-guided design and component-based synthesis are used to produce iboxamycin, a novel ribosome-binding antibiotic with potent activity against Gram-positive and Gram-negative bacteria.
- Matthew J. Mitcheltree
- , Amarnath Pisipati
- & Andrew G. Myers
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News & Views |
Benzene rings broken for chemical synthesis
Benzene rings are almost unbreakable in typical reaction conditions. Chemistry has now been developed that selectively breaks these rings open, highlighting their potential as building blocks for making open-chain molecules.
- Mark R. Crimmin
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Article |
Enantioselective synthesis of ammonium cations
Enantioselective supramolecular recognition allows for the asymmetric synthesis of nitrogen stereocentres, providing chiral ammonium cations in a dynamic crystallization process.
- Mark P. Walsh
- , Joseph M. Phelps
- & Matthew O. Kitching
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News & Views |
Direct installation of boron groups offers boost to medicinal chemistry
Compounds called borylated azines have untapped potential for organic synthesis, but have faced problems associated with their preparation, stability and reactivity. A new class of these compounds provides a solution.
- Christine M. Le
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Article |
Cleaving arene rings for acyclic alkenylnitrile synthesis
Common aromatic rings, such as anilines, arylboronic acids and aryl halides, can be opened up and converted to alkenyl nitriles through carbon–carbon bond cleavage using a copper catalyst.
- Xu Qiu
- , Yueqian Sang
- & Ning Jiao
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Article |
Photoinduced copper-catalysed asymmetric amidation via ligand cooperativity
In the presence of three ligands and light, two distinct copper catalysts combine to produce enantioenriched secondary amides from racemic alkyl electrophiles and primary amide nucleophiles.
- Caiyou Chen
- , Jonas C. Peters
- & Gregory C. Fu
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News & Views |
Nitrogen deletion offers fresh strategy for organic synthesis
Many scientific fields and industries rely on the synthesis of small organic molecules. A chemical reagent has been developed that allows such molecules to be made by ‘deleting’ nitrogen atoms from readily accessible precursors.
- William P. Unsworth
- & Alyssa-Jennifer Avestro
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News & Views |
Highly reactive form of magnesium stabilized by bulky ligands
Magnesium atoms typically lose two electrons to form chemical compounds. A reactive complex has finally been made in which magnesium keeps all of its electrons, and which can be thought of as a soluble form of the metal.
- Cameron Jones
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Article |
Phosphorus-mediated sp2–sp3 couplings for C–H fluoroalkylation of azines
Bench-stable fluoroalkylphosphine reagents are used to form C–CF2X bonds in a one-pot process, reliably fluoroalkylating pyridine building blocks and drug and agrochemical intermediates.
- Xuan Zhang
- , Kyle G. Nottingham
- & Andrew McNally
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Article |
Strongly reducing magnesium(0) complexes
Strongly reducing β-diketiminate complexes containing magnesium in its zero oxidation state are reported, among which is a compound with a linear triatomic Mg–Mg–Mg core.
- B. Rösch
- , T. X. Gentner
- & S. Harder
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News & Views |
High-performance plastic made from renewable oils is chemically recyclable by design
Plastics are invaluable materials, but they use up petroleum resources and persist in the environment. A high-performance plastic derived from renewable oils has been designed at the molecular level to be truly recyclable.
- Charlotte K. Williams
- & Georgina L. Gregory
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Article |
Closed-loop recycling of polyethylene-like materials
Polycarbonates and polyesters with materials properties like those of high-density polyethylene can be recycled chemically by depolymerization to their constituent monomers, re-polymerization yielding material with uncompromised processing and materials properties.
- Manuel Häußler
- , Marcel Eck
- & Stefan Mecking
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News & Views |
Machine learning made easy for optimizing chemical reactions
An accessible machine-learning tool has been developed that can accelerate the optimization of a wide range of synthetic reactions — and reveals how cognitive bias might have undermined optimization by humans.
- Jason E. Hein
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Article |
Bayesian reaction optimization as a tool for chemical synthesis
Bayesian optimization is applied in chemical synthesis towards the optimization of various organic reactions and is found to outperform scientists in both average optimization efficiency and consistency.
- Benjamin J. Shields
- , Jason Stevens
- & Abigail G. Doyle
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Article |
Computational planning of the synthesis of complex natural products
A synthetic route-planning algorithm, augmented with causal relationships that allow it to strategize over multiple steps, can design complex natural-product syntheses that are indistinguishable from those designed by human experts.
- Barbara Mikulak-Klucznik
- , Patrycja Gołębiowska
- & Bartosz A. Grzybowski
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News & Views |
Modular synthesis enables molecular ju-jitsu in the fight against antibiotic resistance
An ancient resistance mechanism poses a problem when using streptogramin antibiotics. A modular approach to drug synthesis exploits this same mechanism to generate an antibiotic that avoids the emergence of resistance.
- Daniel J. Blair
- & Martin D. Burke
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Article |
Synthetic group A streptogramin antibiotics that overcome Vat resistance
Modular synthesis and structural biology are used to design and characterize group A streptogramin antibiotics, one of which has activity against streptogramin-resistant strains and demonstrates efficacy in a mouse model of bacterial infection.
- Qi Li
- , Jenna Pellegrino
- & Ian B. Seiple
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Article |
Intercepting fleeting cyclic allenes with asymmetric nickel catalysis
Asymmetric nickel catalysis is used to intercept transient cyclic allene intermediates to achieve stereocontrol.
- Michael M. Yamano
- , Andrew V. Kelleghan
- & Neil K. Garg
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News & Views |
Reactions for making widely used aniline compounds break norms of synthesis
Chemists generally regard benzene rings as preformed units that are elaborated to build larger molecules. This idea has now been challenged in reactions for making anilines — precursors of many high-value chemical products.
- Valerie A. Schmidt
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Article |
Deep strong light–matter coupling in plasmonic nanoparticle crystals
Photons and plasmons hybridize into polaritons in three-dimensional crystals of plasmonic nanoparticles, leading to deep strong light–matter coupling and the breakdown of the Purcell effect.
- Niclas S. Mueller
- , Yu Okamura
- & Stephanie Reich
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Article |
Fluorescent bicolour sensor for low-background neutrinoless double β decay experiments
A fluorescent bicolour sensor is proposed as the basis of a barium-tagging technique for the detection of neutrinoless double β decay in xenon gas experiments.
- Iván Rivilla
- , Borja Aparicio
- & Juan J. Gómez-Cadenas
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Article |
Preparation of cyclohexene isotopologues and stereoisotopomers from benzene
Cyclohexene isotopologues and stereoisotopomers with varying degrees of deuteration are formed by binding a tungsten complex to benzene, which facilitates the selective incorporation of deuterium into any position on the ring.
- Jacob A. Smith
- , Katy B. Wilson
- & W. Dean Harman
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News |
Cyber-spinach turns sunlight into sugar
Combination of biological membrane and artificial chemistry could power future synthetic organisms.
- Colin Barras
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News & Views |
Manganese catalyst enables exploration of the magic methyl effect
The addition of a methyl group to a drug molecule can greatly alter the drug’s pharmacological properties. A catalyst has been developed that enables this ‘magic methyl effect’ to be rapidly explored for drug discovery.
- Emily B. Corcoran
- & Danielle M. Schultz
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News & Views |
Strong chemical reducing agents produced by light
An electrically neutral radical has been found to be a potent chemical reducing agent when excited by light. Remarkably, it is produced from a positively charged precursor that has long been used as a strong excited-state oxidizing agent.
- Radek Cibulka
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Article |
Automated radial synthesis of organic molecules
An automated synthesis instrument comprising a series of continuous flow modules that are radially arranged around a central switching station can achieve both linear and convergent syntheses.
- Sourav Chatterjee
- , Mara Guidi
- & Kerry Gilmore
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News & Views |
Radial flow system decouples reactions in automated synthesis of organic molecules
Organic compounds can be synthesized in a continuous flow of solutions, but the need to balance mass flow across multiple reactors complicates the development of such systems. A new platform for flow chemistry addresses this issue.
- Klavs F. Jensen
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Article |
Late-stage oxidative C(sp3)–H methylation
A manganese-catalysed oxidative C(sp3)–H methylation method allows a methyl group to be selectively installed into medicinally important heterocycles, providing a way to improve pharmaceuticals and better understand the ‘magic methyl effect’.
- Kaibo Feng
- , Raundi E. Quevedo
- & M. Christina White
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Article |
Gram-scale bottom-up flash graphene synthesis
Flash Joule heating of inexpensive carbon sources is used to produce gram-scale quantities of high-quality graphene in under a second, without the need for a furnace, solvents or reactive gases.
- Duy X. Luong
- , Ksenia V. Bets
- & James M. Tour
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Article |
Design and synthesis of multigrain nanocrystals via geometric misfit strain
Heteroepitaxy is used to precisely control the growth of Mn3O4 shells on the faces of a Co3O4 nanocube crystal, producing uniform grain boundary defects and highly ordered multigrain nanostructures.
- Myoung Hwan Oh
- , Min Gee Cho
- & Taeghwan Hyeon
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Article |
Confinement of atomically defined metal halide sheets in a metal–organic framework
The pore space in the metal–organic framework Zr6O4(OH)4(bpydc)6 can be used as a scaffold to grow precisely defined atomically thick sheets of metal halide materials, taking advantage of multiple binding sites to direct complexation of the metal ions; these metal halide nanosheets fill the size gap between discrete molecular magnets and bulk magnetic materials, with potentially unusual magnetic properties arising from this size regime.
- Miguel I. Gonzalez
- , Ari B. Turkiewicz
- & Jeffrey R. Long
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Article |
Concise asymmetric synthesis of (−)-bilobalide
A synthetic route to the Ginkgo biloba metabolite (−)-bilobalide is described.
- Meghan A. Baker
- , Robert M. Demoret
- & Ryan A. Shenvi
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News & Views |
Double-click enables synthesis of chemical libraries for drug discovery
Operationally simple chemical reactions, termed click reactions, are widely used in many scientific fields. A streamlined synthesis of compounds called azides looks set to expand the role of click chemistry still further.
- Joseph J. Topczewski
- & En-Chih Liu
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Article |
Metal-free directed sp2-C–H borylation
A method for the site-selective C–H borylation of arenes and heteroarenes is described, in which BBr3 acts as both a reagent and a catalyst.
- Jiahang Lv
- , Xiangyang Chen
- & Zhuangzhi Shi
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Letter |
A 16-step synthesis of the isoryanodane diterpene (+)-perseanol
The chemical synthesis of (+)-perseanol, a diterpene with potent insecticidal properties, is reported.
- Arthur Han
- , Yujia Tao
- & Sarah E. Reisman
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Letter |
Anthropogenic biases in chemical reaction data hinder exploratory inorganic synthesis
Human scientists make unrepresentative chemical reagent and reaction condition choices, and machine-learning algorithms trained on human-selected experiments are less capable of successfully predicting reaction outcomes than those trained on randomly generated experiments.
- Xiwen Jia
- , Allyson Lynch
- & Joshua Schrier
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Letter |
Hindered dialkyl ether synthesis with electrogenerated carbocations
A route to the synthesis of hindered ethers is developed, in which electrochemical oxidation is used to liberate high-energy carbocations that are then captured by an alcohol.
- Jinbao Xiang
- , Ming Shang
- & Phil S. Baran
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Letter |
Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas
N-trifluoromethyl analogues of amides and related carbonyl compounds are prepared via bench-stable carbamoyl fluoride building blocks.
- Thomas Scattolin
- , Samir Bouayad-Gervais
- & Franziska Schoenebeck
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News & Views |
Two-dimensional polymer knits together and unravels in an electric field
The tip of a scanning tunnelling microscope has been used to convert a molecular assembly into a 2D polymer and back, at room temperature — revealing how extreme environmental conditions can alter the progress of reactions.
- Markus Lackinger
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News & Views |
Holistic models of reaction selectivity
Computational models that predict the selectivity of reactions are typically accurate for only a specific reaction type and a narrow range of reaction components. A more general model has now been reported.
- Per-Ola Norrby
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Perspective |
The digitization of organic synthesis
This Perspective discusses the challenges associated with the prediction of chemical synthesis, in particular the reaction conditions required for organic transformations, and the role of machine-learning approaches in the prediction process.
- Ian W. Davies
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Letter |
Quaternary-centre-guided synthesis of complex polycyclic terpenes
An approach in which quaternary centres are leveraged to improve synthetic planning can lead to shorter and optimized syntheses, demonstrated here on a series of polycyclic terpenes.
- Pengfei Hu
- , Hyung Min Chi
- & Scott A. Snyder
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Letter |
Site-selective and versatile aromatic C−H functionalization by thianthrenation
A highly site-selective aromatic C–H functionalization reaction that does not require a particular directing group or arene substitution pattern provides functionalized arenes that can participate in various transformations.
- Florian Berger
- , Matthew B. Plutschack
- & Tobias Ritter
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News & Views |
Machine learning speeds up synthesis of porous materials
Failed chemical reactions are often not reported, which means that vast amounts of potentially useful data are going to waste. Experiments show that machine learning can use such data to optimize the preparation of porous materials.
- Seth Cohen
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News Feature |
Extreme chemistry: experiments at the edge of the periodic table
As the chase for new elements slows, scientists focus on deepening their understanding of the superheavy ones they already know.
- Philip Ball
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News & Views |
Practically simple reactions convert hydrocarbons to precious chemicals
Operationally simple chemistry enables aliphatic carbon–carbon bonds — the ‘girders’ in the framework of many organic molecules — to be prepared from widely available hydrocarbons known as alkenes.
- James P. Morken
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Letter |
Deconstructive diversification of cyclic amines
The silver-mediated deconstructive functionalization of saturated nitrogen heterocycles via acylic haloamine intermediates provides access to various acyclic amines as well as enabling ring contraction and skeletal remodelling.
- Jose B. Roque
- , Yusuke Kuroda
- & Richmond Sarpong
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Letter |
Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides
This nickel-catalysed Suzuki–Miyaura coupling of aryl boronic acids with in-situ-generated acid fluorides does not require an exogenous base and is applicable to a range of base-sensitive boronic acids and bioactive carboxylic acids.
- Christian A. Malapit
- , James R. Bour
- & Melanie S. Sanford
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