Featured
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Letter |
Asymmetric α-arylation of amino acids
This approach introduces an aryl substituent to the α-carbon of amino acids without a transition-metal catalyst, and uses the inherent chirality of the amino acid itself as the source of asymmetry.
- Daniel J. Leonard
- , John W. Ward
- & Jonathan Clayden
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Letter |
Building C(sp3)-rich complexity by combining cycloaddition and C–C cross-coupling reactions
Combining cycloaddition and carbon–carbon cross-coupling offers a way of simplifying the enantioselective preparation of chemical building blocks, natural products and medicines such as the antipsychotic asenapine.
- Tie–Gen Chen
- , Lisa M. Barton
- & Phil S. Baran
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Review Article |
Machine learning for molecular and materials science
Recent progress in machine learning in the chemical sciences and future directions in this field are discussed.
- Keith T. Butler
- , Daniel W. Davies
- & Aron Walsh
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Letter |
Controlling an organic synthesis robot with machine learning to search for new reactivity
A robot instructed by a machine learning algorithm and coupled with real-time spectroscopic systems provides fast and accurate reaction outcome predictions and reactivity assessments, leading to the discovery of new reactions.
- Jarosław M. Granda
- , Liva Donina
- & Leroy Cronin
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Letter |
Nanoscale synthesis and affinity ranking
A system that combines nanoscale synthesis and affinity ranking enables high-throughput screening of reaction conditions and bioactivity for a given protein target, accelerating the process of drug discovery.
- Nathan J. Gesmundo
- , Bérengère Sauvagnat
- & Tim Cernak
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News & Views |
Peptides used to make light-twisting nanoparticles
The growth of gold nanoparticles has been manipulated using amino acids and peptides to produce twisted structures that alter the rotation of light. The method could simplify the development of optical devices.
- Guillermo González-Rubio
- & Luis M. Liz-Marzán
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Letter |
Amino-acid- and peptide-directed synthesis of chiral plasmonic gold nanoparticles
Chirality can be ‘encoded’ into gold nanoparticles by introducing chiral amino acids or peptides during the growth process, leading to the formation of helicoid morphologies.
- Hye-Eun Lee
- , Hyo-Yong Ahn
- & Ki Tae Nam
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News |
Attacks in UK and Syria highlight growing need for chemical-forensics expertise
Nations seek to better address future chemical-weapons threats.
- Declan Butler
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Article |
Planning chemical syntheses with deep neural networks and symbolic AI
Deep neural networks and Monte Carlo tree search can plan chemical syntheses by training models on a huge database of published reactions; their predicted synthetic routes cannot be distinguished from those a human chemist would design.
- Marwin H. S. Segler
- , Mike Preuss
- & Mark P. Waller
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News |
Need to make a molecule? Ask this AI for instructions
Artificial-intelligence tool that has digested nearly every reaction ever performed could transform chemistry.
- Holly Else
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Letter |
Generating carbyne equivalents with photoredox catalysis
A photocatalytic strategy is described that generates diazomethyl radicals as direct equivalents of carbynes, which are often too reactive to use, enabling the functionalization of a range of medically useful compounds.
- Zhaofeng Wang
- , Ana G. Herraiz
- & Marcos G. Suero
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News & Views |
Reactive carbon species tamed for synthesis
A highly reactive form of carbon, known as a carbyne, holds great promise for organic synthesis, but has been difficult to prepare. Reactions that produce carbyne equivalents now unleash this synthetic potential.
- Rohan E. J. Beckwith
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Letter |
Site-selective and stereoselective functionalization of non-activated tertiary C–H bonds
The functionalization of specific inert C–H bonds avoids the need for functional groups in organic synthesis and here the challenges of this approach are overcome using a dirhodium catalyst that is capable of C–H bond site-selectivity.
- Kuangbiao Liao
- , Thomas C. Pickel
- & Huw M. L. Davies
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Technology Feature |
Check your chemistry
Chemical probes and screening libraries can easily get mixed up or messed up, causing misleading results for unwary biologists.
- Monya Baker
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Letter |
Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide
A nickel catalyst that promotes carboxylation of halogenated hydrocarbons at remote aliphatic sites with carbon dioxide via tunable and controllable chain-walking is described.
- Francisco Juliá-Hernández
- , Toni Moragas
- & Ruben Martin
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News |
Elusive triangulene created by moving atoms one at a time
Unstable molecule couldn’t be made through conventional synthesis, so IBM researchers carried out molecular surgery using a microscope tip.
- Philip Ball
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Research Highlights |
Bacteria in humans yield drug
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Letter |
Amide-directed photoredox-catalysed C–C bond formation at unactivated sp3 C–H bonds
The formation of carbon–carbon bonds is achieved via directed cleavage of traditionally non-reactive carbon–hydrogen bonds and their subsequent coupling with readily available alkenes.
- John C. K. Chu
- & Tomislav Rovis
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News & Views |
Sixty years of living polymers
In the 1950s, the discovery of a class of 'living' polymerization reaction revolutionized the field of polymer science by providing a way of controlling the molecular-weight distribution of polymers. The effects reverberate to this day.
- Gary Patterson
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Letter |
Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups
A difficult synthesis is described that uses an organocopper catalyst and commercially available starting materials to give high yield and the mechanics of the reaction are elucidated through density functional theory.
- Fanke Meng
- , Xiben Li
- & Amir H. Hoveyda
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News |
Hundreds of antibiotics built from scratch
Chemists generate variations on erythromycin in ‘daring’ synthesis.
- Heidi Ledford
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News & Views |
Fighting evolution with chemical synthesis
A synthetic strategy has been developed that provides easy access to structurally diverse analogues of naturally occurring antibiotics, providing a fresh means of attack in the war against drug-resistant bacteria. See Article p.338
- Ming Yan
- & Phil S. Baran
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Letter |
Concerted nucleophilic aromatic substitution with 19F− and 18F−
Nucleophilic aromatic substitution (SNAr) is the most commonly used method to generate arenes that contain 18F for use in PET imaging; here, an unusual concerted SNAr reaction is presented that is not limited to electron-poor arenes.
- Constanze N. Neumann
- , Jacob M. Hooker
- & Tobias Ritter
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Letter |
Site-selective and stereoselective functionalization of unactivated C–H bonds
The idea of carbon–hydrogen functionalization, in which C–H bonds are modified at will, represents a paradigm shift in the standard logic of organic synthesis; here, dirhodium catalysts are used to achieve highly site-selective, diastereoselective and enantioselective C–H functionalization of n-alkanes and terminally substituted n-alkyl compounds.
- Kuangbiao Liao
- , Solymar Negretti
- & Huw M. L. Davies
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News & Views |
No double bond left behind
Alkenyl halides are some of the most useful building blocks for synthesizing small organic molecules. A catalyst has now allowed their direct preparation from widely available alkenes using the cross-metathesis reaction. See Article p.459
- David Sarlah
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Letter |
Nineteen-step total synthesis of (+)-phorbol
Enantiospecific total synthesis of (+)-phorbol in only 19 steps from the abundant monoterpene (+)-3-carene is demonstrated using a two-phase terpene synthesis strategy.
- Shuhei Kawamura
- , Hang Chu
- & Phil S. Baran
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Article |
Network-analysis-guided synthesis of weisaconitine D and liljestrandinine
WebNetwork analysis to determine the maximally bridged ring (or rings) of molecules is used as part of a strategy for the syntheses of architecturally complex natural chemicals; this strategy is demonstrated via the synthesis of the diterpenoid alkaloids weisaconitine D and liljestrandinine.
- C. J. Marth
- , G. M. Gallego
- & R. Sarpong
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Letter |
Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates
A new method for catalysing the cross-coupling of two different aryl electrophiles is described; the principle of this method, which involves cooperation between two metal catalysts that are selective towards different substrates, should be generally useful in catalysis.
- Laura K. G. Ackerman
- , Matthew M. Lovell
- & Daniel J. Weix
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News & Views |
A cure for catalyst poisoning
Compounds that are sensitive to the components of air are difficult to use in chemical reactions, requiring conditions that are tedious to set up. A simple, practical solution to this problem has finally been devised. See Letter p.208
- Marcus E. Farmer
- & Phil S. Baran
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Letter |
Dosage delivery of sensitive reagents enables glove-box-free synthesis
A method of supplying exactly the amounts of air- and moisture-sensitive catalysts and ligands needed for three commonly used syntheses in a stable, storable form in a sealed capsule is described; it should reduce the unnecessary waste of chemicals, money and time.
- Aaron C. Sather
- , Hong Geun Lee
- & Stephen L. Buchwald
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News & Views |
Natural polarity inverted
The concept of umpolung describes the reversal of the naturally occurring electrostatic polarization of chemical groups. It has now been used to make single mirror-image isomers of nitrogen-containing molecules. See Letter p.445
- Fedor Romanov-Michailidis
- & Tomislav Rovis
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News & Views |
Streamlining drug synthesis
Drug manufacture can benefit from flow synthesis, in which raw materials are fed into a sequence of reactors, producing the drug as a continuous output. A flow strategy that capitalizes on solid catalysts has now been realized. See Letter p.329
- Joel M. Hawkins
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Letter |
Multistep continuous-flow synthesis of (R)- and (S)-rolipram using heterogeneous catalysts
The continuous-flow synthesis of both enantiomers of a complex molecule, the anti-inflammatory drug rolipram, is described, using only columns packed with achiral and chiral heterogeneous catalysts, thus enabling batch processing to be avoided.
- Tetsu Tsubogo
- , Hidekazu Oyamada
- & Shū Kobayashi
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News |
Complex molecules made to order in synthesis machine
Automated clipping together of modular building blocks shows promise for drug discovery.
- Katharine Sanderson
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Article |
Multifunctional organoboron compounds for scalable natural product synthesis
A catalytic process is reported that begins with a highly selective copper–boron addition to a monosubstituted allene, and in which the resulting boron-substituted organocopper intermediate then participates in a chemoselective, site-selective and enantioselective allylic substitution; this approach is used in the enantioselective synthesis of gram quantities of two natural products.
- Fanke Meng
- , Kevin P. McGrath
- & Amir H. Hoveyda
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Review Article |
An overview of N-heterocyclic carbenes
N-heterocyclic carbenes are powerful tools in organic chemistry, with many commercially important applications; this overview describes their properties and potential uses.
- Matthew N. Hopkinson
- , Christian Richter
- & Frank Glorius
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Letter |
Palladium-catalysed C–H activation of aliphatic amines to give strained nitrogen heterocycles
A palladium-catalysed C–H bond activation process is reported that proceeds through a four-membered-ring cyclopalladation pathway; it allows a methyl group that is adjacent to an unprotected secondary amine to be transformed into a synthetically versatile nitrogen heterocycle.
- Andrew McNally
- , Benjamin Haffemayer
- & Matthew J. Gaunt
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Article |
Total synthesis and isolation of citrinalin and cyclopiamine congeners
Natural products citrinalin B and cyclopiamine B, which contain basic nitrogen atoms that are susceptible to oxidation during synthesis, can be synthesized by the selective introduction and removal of functional groups.
- Eduardo V. Mercado-Marin
- , Pablo Garcia-Reynaga
- & Richmond Sarpong
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Letter |
Alkane desaturation by concerted double hydrogen atom transfer to benzyne
Benzynes are capable of concerted removal of two vicinal hydrogen atoms from a hydrocarbon, a discovery enabled by the thermal generation of reactive benzyne intermediates through the hexadehydro-Diels–Alder cycloisomerization reaction of triyne substrates.
- Dawen Niu
- , Patrick H. Willoughby
- & Thomas R. Hoye
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Letter |
Controlled-reflectance surfaces with film-coupled colloidal nanoantennas
Randomly adsorbing chemically synthesized silver nanocubes, each of which is the optical analogue of a grounded patch antenna, onto a nanoscale-thick polymer spacer layer on a gold film results in a metamaterial surface with a reflectance spectrum that can be tailored by varying the geometry.
- Antoine Moreau
- , Cristian Ciracì
- & David R. Smith
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Letter |
Practical and innate carbon–hydrogen functionalization of heterocycles
It is shown that zinc sulphinate salts can be used to transfer alkyl radicals to heterocycles, allowing for the mild, direct and operationally simple formation of medicinally relevant carbon–carbon bonds while reacting in a complementary fashion to other innate carbon–hydrogen functionalization methods.
- Yuta Fujiwara
- , Janice A. Dixon
- & Phil S. Baran
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Research Highlights |
Mega-MOF's super surface
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Letter |
Spontaneous motion in hierarchically assembled active matter
Active materials are hierarchically assembled, starting from extensile microtubule bundles, to form emulsions with unexpected collective biomimetic properties such as autonomous motility.
- Tim Sanchez
- , Daniel T. N. Chen
- & Zvonimir Dogic
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News & Views |
Single molecules put a ring on it
A variant of a classical reaction has been used to generate short-lived chemical species called arynes, allowing the one-step synthesis of structurally complex benzene derivatives from simple precursors. See Article p.208
- John T. S. Yeoman
- & Sarah E. Reisman
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Article |
Watching DNA polymerase η make a phosphodiester bond
Atomic-resolution time courses of phosphodiester bond formation catalysed by DNA polymerase η reveal transient intermediate states and an unexpected third metal ion in the reaction mechanism.
- Teruya Nakamura
- , Ye Zhao
- & Wei Yang
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Letter |
Direct and highly regioselective and enantioselective allylation of β-diketones
A simple, regioselective and enantioselective method for allylating β-diketones has been developed, significantly expanding the pool of easily accessible enantiomerically enriched and functionally complex tertiary carbinols.
- Wesley A. Chalifoux
- , Samuel K. Reznik
- & James L. Leighton
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Outlook |
Production: Beyond sticky tape
Flecks of graphene are easy to make. But producing sheets of pristine, electronics-quality material is another matter.
- Richard Van Noorden
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News & Views |
Gold's enigmatic surface
Gold is not as inert as was believed — it can promote molecular synthesis. A study uses scanning tunnelling microscopy to catch gold in the act as it guides the formation of one-dimensional polymers from saturated hydrocarbons.
- Robert J. Madix
- & Cynthia M. Friend
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Letter |
Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis
- Miao Yu
- , Chenbo Wang
- & Amir H. Hoveyda
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