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Hydrogen-bond-acceptor ligands enable distal C(sp3)–H arylation of free alcohols
Ligands enable alcohol-directed arylation of δ-C(sp3)–H bonds by stabilizing hydroxyl coordination to palladium through charge balance and hydrogen bonding.
- Daniel A. Strassfeld
- , Chia-Yu Chen
- & Jin-Quan Yu
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Article |
Quinone-mediated hydrogen anode for non-aqueous reductive electrosynthesis
A quinone-mediated hydrogen anode design shows that hydrogen can be used as the electron source in non-aqueous reductive electrosynthesis, for a more sustainable way to make molecules at larger scale.
- Jack Twilton
- , Mathew R. Johnson
- & Shannon S. Stahl
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General cross-coupling reactions with adaptive dynamic homogeneous catalysis
A self-adjustive catalytic system with nickel under visible-light-driven redox reaction conditions provides a general method for carbon–(hetero)atom cross-coupling reactions and is demonstrated for nine different bond-forming reactions.
- Indrajit Ghosh
- , Nikita Shlapakov
- & Burkhard König
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Transannular C–H functionalization of cycloalkane carboxylic acids
Quinuclidine-pyridone and sulfonamide-pyridone ligands enable transannular γ-methylene C–H arylation of cycloalkane carboxylic acids with a range of ring sizes, bringing us closer to molecular editing of saturated carbocycles.
- Guowei Kang
- , Daniel A. Strassfeld
- & Jin-Quan Yu
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Article
| Open AccessCatalytic disconnection of C–O bonds in epoxy resins and composites
The authors report a transition-metal-catalysed protocol for recovery of polymer building block bisphenol A and intact fibres from epoxy composites, demonstrating that chemical recycling approaches for thermoset epoxy resins and composites are achievable.
- Alexander Ahrens
- , Andreas Bonde
- & Troels Skrydstrup
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Article |
Selective methane oxidation by molecular iron catalysts in aqueous medium
Methane can be oxidized to methanol using N-heterocyclic carbene-ligated FeII complexes, in which the hydrophobic cavity captures the methane substrate from an aqueous solution and releases the hydrophilic methanol product back into the solution.
- Hiroto Fujisaki
- , Tomoya Ishizuka
- & Takahiko Kojima
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Article |
Copper-catalysed enantioconvergent alkylation of oxygen nucleophiles
The enantioconvergent alkylation of oxygen nucleophiles is achieved using α-haloamides and a readily available copper catalyst, and the reaction proceeds under mild conditions in the presence of a wide variety of functional groups.
- Caiyou Chen
- & Gregory C. Fu
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Article
| Open AccessCatalytic synthesis of phenols with nitrous oxide
A study demonstrates that nitrous oxide can act as the source of O in a catalytic conversion of aryl halides to phenols, releasing N2 as by-product.
- Franck Le Vaillant
- , Ana Mateos Calbet
- & Josep Cornella
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Article
| Open AccessTritiation of aryl thianthrenium salts with a molecular palladium catalyst
The isotopic label tritium can be selectively added into aromatic organic compounds by a homogenous hydrogenolysis reaction using aryl thianthrenium salts, tritium gas and a molecular palladium catalyst.
- Da Zhao
- , Roland Petzold
- & Tobias Ritter
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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 |
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 |
Desymmetrization of difluoromethylene groups by C–F bond activation
Enantioselective activation of a single C–F bond in a difluoromethylene group is achieved using a chiral transition metal catalyst and a fluorophilic activator.
- Trevor W. Butcher
- , Jonathan L. Yang
- & John F. Hartwig
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Article |
Synthesis of rare sugar isomers through site-selective epimerization
Various rare sugars that cannot be isolated from natural sources are synthesized using light-driven epimerization, a process which may find application in other synthetic scenarios.
- Yong Wang
- , Hayden M. Carder
- & Alison E. Wendlandt
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Article |
Lactonization as a general route to β-C(sp3)–H functionalization
Pd-catalysed β-C(sp3)–H lactonization of aliphatic acids enabled by a mono-N-protected β-amino acid and tert-butyl hydrogen peroxide is reported, achieving high β-position selectivity without the use of a directing group.
- Zhe Zhuang
- & Jin-Quan Yu
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Letter |
Deacylative transformations of ketones via aromatization-promoted C–C bond activation
Aromatization-driven C–C bond activation through iridium/phosphine catalysis enables deacylative transformations in various ketone substrates.
- Yan Xu
- , Xiaotian Qi
- & Guangbin Dong
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Letter |
Cooperative asymmetric reactions combining photocatalysis and enzymatic catalysis
A cooperative chemoenzymatic reaction combines photocatalytic alkene isomerization with enzymatic reduction to generate enantioenriched products in a stereoconvergent manner.
- Zachary C. Litman
- , Yajie Wang
- & John F. Hartwig
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Letter |
Palladium-catalysed electrophilic aromatic C–H fluorination
An approach for the direct electrophilic C–H fluorination of arenes is reported, using a palladium catalyst and mild fluorinating reagents.
- Kumiko Yamamoto
- , Jiakun Li
- & Tobias Ritter
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Letter |
Ligand-accelerated non-directed C–H functionalization of arenes
Using a ligand as a promoter enhances the reactivity of the palladium catalyst in non-directed C–H functionalization of arenes, enabling the arene to be used as the limiting reagent.
- Peng Wang
- , Pritha Verma
- & Jin-Quan Yu
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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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Letter |
Decarboxylative alkenylation
Starting with alkyl carboxylic acids, a simple olefin synthesis using any substitution pattern or geometry, based on amide-bond synthesis with nickel- or iron-based catalysis, is described.
- Jacob T. Edwards
- , Rohan R. Merchant
- & Phil S. Baran
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Letter |
Catalytic activation of carbon–carbon bonds in cyclopentanones
In the chemical industry, it is often necessary to activate carbon–carbon bonds in order to synthesize complex organic molecules, but this is challenging when starting with simple five- or six-membered carbon rings; a new method uses a rhodium pre-catalyst and an amino-pyridine co-catalyst, enabling an overall energetically favourable reaction that involves activation of carbon–carbon bonds plus activation of carbon–hydrogen bonds.
- Ying Xia
- , Gang Lu
- & Guangbin Dong
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Letter |
Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators
A co-catalyst system for electrochemical alcohol oxidation composed of a bipyridine copper catalyst and an electron-proton-transfer mediator called TEMPO operates at much lower potential and is faster than TEMPO alone.
- Artavazd Badalyan
- & Shannon S. Stahl
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Letter |
Iron(III)-catalysed carbonyl–olefin metathesis
The olefin metathesis reaction of two unsaturated substrates is one of the most powerful carbon–carbon-bond-forming reactions in organic chemistry; here, a catalytic carbonyl–olefin ring-closing metathesis reaction is demonstrated that uses iron, an abundant and environmentally benign metal, as a catalyst.
- Jacob R. Ludwig
- , Paul M. Zimmerman
- & Corinna S. Schindler
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Letter |
Palladium-catalysed transannular C–H functionalization of alicyclic amines
An approach to selectively manipulate the C–H bonds of alicyclic amines at sites remote to nitrogen is demonstrated by the synthesis of new derivatives of several bioactive molecules, including varenicline, a drug used to treat nicotine addiction.
- Joseph J. Topczewski
- , Pablo J. Cabrera
- & Melanie S. Sanford
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Review Article |
Recent advances in homogeneous nickel catalysis
Some of the most recent and significant developments in homogeneous nickel catalysis are reviewed, including nickel-mediated cross-coupling reactions and carbon–hydrogen bond activation reactions.
- Sarah Z. Tasker
- , Eric A. Standley
- & Timothy F. Jamison