Featured
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Article |
A deconstruction-reconstruction strategy for pyrimidine diversification
- Benjamin J. H. Uhlenbruck
- , Celena M. Josephitis
- & Andrew McNally
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Article |
Observing the primary steps of ion solvation in helium droplets
The initial steps of the ion solvation process are observed for the solvation of a single sodium ion in liquid helium, opening possibilities for benchmarking theoretical descriptions of ion solvation.
- Simon H. Albrechtsen
- , Constant A. Schouder
- & Henrik Stapelfeldt
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Article |
Carbon-to-nitrogen single-atom transmutation of azaarenes
A new type of transformation converting a heteroaromatic carbon atom into a nitrogen atom, turning quinolines into quinazolines to enable manipulation of molecular properties, is reported.
- Jisoo Woo
- , Colin Stein
- & Mark D. Levin
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Article |
Geminal-atom catalysis for cross-coupling
Heterogeneous geminal-atom catalysts, which pair single-atom sites in specific coordination and spatial proximity, offer a new avenue for the sustainable manufacture of fine chemicals.
- Xiao Hai
- , Yang Zheng
- & Jiong Lu
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Article |
Regioselective aliphatic C–H functionalization using frustrated radical pairs
Regioselective functionalization of aliphatic carbon–hydrogen bonds is achieved using frustrated radical pairs generated from disilazide donors and an N-oxoammonium acceptor.
- Zhipeng Lu
- , Minsoo Ju
- & Song Lin
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Article
| Open Access
Control of stereogenic oxygen in a helically chiral oxonium ion
The design, synthesis and characterization of a helically chiral triaryloxonium ion is reported, which is an example of a chiral non-racemic and configurationally stable molecule in which the oxygen atom is the sole stereogenic centre.
- Owen Smith
- , Mihai V. Popescu
- & Martin D. Smith
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Article |
Organic reaction mechanism classification using machine learning
Mechanistic elucidation through currently available kinetic analysis is limited by mathematical approximations and human interpretation, here a deep neural network model has been trained to analyse ordinary kinetic data and automatically elucidate the corresponding mechanism class.
- Jordi Burés
- & Igor Larrosa
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Article
| Open Access
Condensed-phase isomerization through tunnelling gateways
Measurements of isomerization rates of CO isotopologues on an NaCl surface show a nonmonotonic mass dependence that arises from resonantly enhanced cross-barrier coupling, or ‘tunnelling gateways’, which are intrinsic to condensed-phase tunnelling.
- Arnab Choudhury
- , Jessalyn A. DeVine
- & Alec M. Wodtke
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Article |
Multicomponent alkene azidoarylation by anion-mediated dual catalysis
A streamlined synthesis of β-arylethylamines using two distinct copper catalysts is reported, and an azide anion is proposed to both react to form the product and facilitate catalyst regeneration.
- Ala Bunescu
- , Yusra Abdelhamid
- & Matthew J. Gaunt
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Article |
Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication
The synthesis of aziridines—three-membered nitrogen-containing heterocycles—is achieved by a new method involving the electrochemical coupling of alkenes and amines, via a dicationic intermediate.
- Dylan E. Holst
- , Diana J. Wang
- & Zachary K. Wickens
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Article |
Skeletal editing through direct nitrogen deletion of secondary amines
Nitrogen is ‘deleted’ from secondary amines using anomeric amide reagents, which react with the amine to form an isodiazene, after which nitrogen gas is released and the resulting carbon radicals combine to form a carbon–carbon bond.
- Sean H. Kennedy
- , Balu D. Dherange
- & Mark D. Levin
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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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Article |
Coupling dinitrogen and hydrocarbons through aryl migration
An iron complex sequentially activates N2 and C–H bonds in benzene to form aniline, with coupling achieved through partial silylation of a reduced iron–nitrogen complex and phenyl migration.
- Sean F. McWilliams
- , Daniël L. J. Broere
- & Patrick L. Holland
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Article |
A general carbonyl alkylative amination for tertiary amine synthesis
The synthesis of tertiary amines is achieved through a carbonyl alkylative amination reaction facilitated by visible light, in which an aldehyde and an amine condense to form an iminium ion that subsequently reacts with alkyl radical.
- Roopender Kumar
- , Nils J. Flodén
- & Matthew J. Gaunt
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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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Article |
Holistic prediction of enantioselectivity in asymmetric catalysis
A workflow for deriving statistical models of one set of reactions that can be used to predict related reactions is presented, facilitating catalyst and enantioselective reaction development.
- Jolene P. Reid
- & Matthew S. Sigman
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Letter |
Enzyme-catalysed [6+4] cycloadditions in the biosynthesis of natural products
Enzymatic catalysis of pericyclic [6+4] cycloaddition reactions to form ten-membered rings is observed during biosynthesis of the macrocyclic antibiotic streptoseomycin, and the mechanism of these transformations is established.
- Bo Zhang
- , Kai Biao Wang
- & Hui Ming Ge
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Review Article |
Exploiting non-covalent π interactions for catalyst design
Our increasing understanding of non-covalent interactions involving aromatic systems is reviewed, and the use of these insights in the design of small-molecule catalysts and enzymes is surveyed.
- Andrew J. Neel
- , Margaret J. Hilton
- & F. Dean Toste
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Letter |
Remote site-selective C–H activation directed by a catalytic bifunctional template
A method is described for selectively activating remote C–H bonds in heterocycles by using a catalytic template that binds by reversible coordination instead of a covalent linkage, removing the need for specific functional groups on which to attach the template.
- Zhipeng Zhang
- , Keita Tanaka
- & Jin-Quan Yu
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Article |
The hexadehydro-Diels–Alder reaction
The de novo generation of benzynes—through a hexadehydro-Diels–Alder reaction—followed by their in situ elaboration is reported; the reaction is metal-free and reagent-free, and reveals new modes of intrinsic benzyne reactivity.
- Thomas R. Hoye
- , Beeraiah Baire
- & Brian P. Woods
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Article |
Regioselective reactions for programmable resveratrol oligomer synthesis
- Scott A. Snyder
- , Andreas Gollner
- & Maria I. Chiriac
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Letter |
Enzyme-catalysed [4+2] cycloaddition is a key step in the biosynthesis of spinosyn A
- Hak Joong Kim
- , Mark W. Ruszczycky
- & Hung-wen Liu
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News & Views |
Fluorination made easier
By putting the pieces of a chemical puzzle into the right order, a thorny problem in catalysis has been solved. This opens the door to syntheses of molecules that contain the useful trifluoromethyl group.
- Tobias Ritter
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Research Highlights |
Chemistry: Metal–organic catalyst
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News & Views |
Amide bonds made in reverse
Amide bonds connect the amino acids in proteins and occur in many other useful molecules. An amide-forming reaction that turns the conventional approach on its head offers a practical way of making these bonds.
- Karl Scheidt
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Letter |
Cleaving carbon–carbon bonds by inserting tungsten into unstrained aromatic rings
The transformation of petroleum-derived feedstocks into useful chemicals often requires controllable cleavage of C–H or C–C bonds. There are many examples of achieving this through the oxidative addition of C–H bonds to metal centres, but analogous transformations of C–C bonds are rare. Here, using a tungsten centre and exploiting the formation of an unusual chelating ligand, a strong C–C bond is cleaved; other metal centres with suitable ancillary ligands could perform the same function.
- Aaron Sattler
- & Gerard Parkin
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Research Highlights |
Chemistry: Chase acid, solve maze
