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Divergent access to 5,6,7-perifused cycles
The lack of efficient and diverse synthesis strategy has hindered the study of perifused cycles. Here, the authors report a metal-catalyzed cascade electrocyclization to access 5,6,7-perifused cycles, and demonstrated the versatility of this protocol in the late-stage modification of pharmaceuticals.
- Jingpeng Han
- , Yongjian Yang
- & Baosheng Li
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Article
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Turning sulfonyl and sulfonimidoyl fluoride electrophiles into sulfur(VI) radicals for alkene ligation
Sulfonyl and sulfonimidoyl fluorides (SFs) are versatile substrates in organic synthesis but conversion to S(VI) radicals is challenging. Here, the authors show that organosuperbase activated SFs can be converted to S(VI) radicals under photocatalytic conditions and demonstrate application of this synthetic pathway in the preparation of functional polymers and dyes.
- Xing Wu
- , Wenbo Zhang
- & Bing Gao
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Doubly N-confused and ring-contracted [24]hexaphyrin Pd-complexes as stable antiaromatic N-confused expanded porphyrins
In the chemistry of porphyrinoids, expanded porphyrins and N-confused porphyrins (NCP) are two important newcomers but antiaromatic expanded NCPs have not been isolated before. Here, the authors report the synthesis of doubly N-confused and ring-contracted hexaphyrin PdII complexes.
- Fuying Luo
- , Le Liu
- & Jianxin Song
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Article
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Sub-second ultrafast yet programmable wet-chemical synthesis
Here the authors present a wet-interfacial Joule heating approach for synthesizing nanomaterials in a sub-second, programmable, and energy/reactant-saving manner, based on the synergy between Joule-heating-based high temperature and evaporation-caused concentration.
- Lin Zhang
- , Li Peng
- & Chao Gao
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Article
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Sustainable production of dopamine hydrochloride from softwood lignin
Efficient production of dopamine direct from lignin is a highly desirable target but extremely challenging. Here, we report an innovative strategy for the sustainable production of dopamine hydrochloride from softwood lignin with a mass yield of 6.4 wt.%.
- Lin Dong
- , Yanqin Wang
- & Zupeng Chen
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Article
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Enantioconvergent construction of stereogenic silicon via Lewis base-catalyzed dynamic kinetic silyletherification of racemic chlorosilanes
Organosilanes bearing an enantioenriched silicon center are important in many fields of chemistry. Here, the authors report a dynamic kinetic silyletherification racemic chlorosilanes with (S)- lactates, leading to asymmetric synthesis of silylethers.
- Tianbao Hu
- , Chen Zhao
- & Zhenlei Song
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Article
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Modular assembly of indole alkaloids enabled by multicomponent reaction
Indole alkaloids are one of the largest alkaloid classes, proving valuable structural moiety in pharmaceuticals but the direct single-step synthesis with broad structural diversity remains challenging. Herein, the authors report a modular assembly of tetrahydrocarboline type of indole alkaloids from simple building blocks in a single step while showing broad compatibility with medicinally relevant functionality
- Jiaming Li
- , Zhencheng Lai
- & Sunliang Cui
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Article
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Machine-learning-assisted material discovery of oxygen-rich highly porous carbon active materials for aqueous supercapacitors
Machine-learning technology provides a data-driven approach to find the critical features for ideal carbon-based supercapacitors. Here, the authors report machine-Learning assisted discovery of oxygen rich highly porous carbons that exhibits a high specific capacitance.
- Tao Wang
- , Runtong Pan
- & Sheng Dai
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Article
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Fluorocarbonylation via palladium/phosphine synergistic catalysis
Despite the growing importance of fluorinated organic compounds introduction of fluorine into organic molecules is still challenging. Here, the authors present the development of palladium and phosphine synergistic redox catalysis of fluorocarbonylation of potassium aryl/alkyl trifluoroborate.
- Mingxin Zhao
- , Miao Chen
- & Pingping Tang
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Article
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Electrochemical synthesis of biaryls by reductive extrusion from N,N’-diarylureas
The synthesis of biaryls by transition metal-free coupling is an important challenge. Here, the authors describe an electrochemical approach to the synthesis of biaryls, in which aniline derivatives are coupled through the temporary formation and reduction of ureas.
- Ellie Stammers
- , Chris D. Parsons
- & Alastair J. J. Lennox
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Article
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Enantioselectivity of discretized helical supramolecule consisting of achiral cobalt phthalocyanines via chiral-induced spin selectivity effect
Experimental realizations of absolute enantioselection, without chiral catalysis or chiral ingredients, has been challenging. Here, the authors obtain enantioselectivity in mesoscale helical supramolecules consisting only of achiral molecules by exploiting chiral-induced spin selectivity (CISS) effect.
- Hiroki Aizawa
- , Takuro Sato
- & Hiroshi M. Yamamoto
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Spin selection in atomic-level chiral metal oxide for photocatalysis
The spin degree of freedom is a key intrinsic parameter for carrier dynamics and surface reaction kinetics in photocatalysis. Here, the authors report a chiral zinc oxide with spin selectivity effect. It can effectively induce spin polarization, thereby promoting electron spin-related redox catalysis.
- Minhua Ai
- , Lun Pan
- & Ji-Jun Zou
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Construction of C-B axial chirality via dynamic kinetic asymmetric cross-coupling mediated by tetracoordinate boron
The application of catalytic dynamic kinetic asymmetric transformation (DyKAT) in axial chirality is limited to fivemembered metalacyclic intermediate-directed equilibrium of substrate enantiomers. Here, the authors report a tetracoordinate boron-directed DyKAT of racemic, configurationally stable 3-bromo- 2,1-azaborines for the construction of C-B axial chirality.
- Kai Yang
- , Yanfei Mao
- & Qiuling Song
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Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors
Catalytic glycosylation provides access to oligosacchairdes with minimal amount of promoters. Here, the authors developed a new catalytic glycosylation reaction using an ester type donor driven by ring-strain release.
- Han Ding
- , Jian Lyu
- & Xue-Wei Liu
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Rapid planning and analysis of high-throughput experiment arrays for reaction discovery
High-throughput experimentation is an increasingly important tool in reaction discovery, while there remains a need for software solutions to navigate data-rich experiments. Here the authors report phactor™, a software that facilitates the performance and analysis of high-throughput experimentation in a chemical laboratory.
- Babak Mahjour
- , Rui Zhang
- & Tim Cernak
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Halide-assisted differential growth of chiral nanoparticles with threefold rotational symmetry
Expanding the library of chiral plasmonic nanoparticles will foster the development of chiroptical applications. Here, the authors apply halide-assisted differential growth to convert Au nanodisks into triskelion-shaped chiral nanoparticles with threefold rotational symmetry.
- Jiapeng Zheng
- , Christina Boukouvala
- & Jianfang Wang
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Article
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A fluorinated cation introduces new interphasial chemistries to enable high-voltage lithium metal batteries
Fluorides have been identified as a key ingredient in interphases supporting aggressive battery chemistries. Here, the authors show a positive charged organic cation carrying fluorine populates at the inner Helmholtz layer of the electrode and contributes to the interphasial chemistry.
- Qian Liu
- , Wei Jiang
- & Zhengcheng Zhang
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Article
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Catalytic asymmetric oxa-Diels–Alder reaction of acroleins with simple alkenes
The asymmetric inverse-electron-demand oxa-Diels–Alder reaction (IODA) between activated α,β-unsaturated carbonyl compounds with highly polarized alkenes has been reported before but acroleins or simple alkenes were so-far rarely employed as substrates. Here, the authors study the catalytic asymmetric intermolecular IODA reaction between acroleins and simple alkenes.
- Lei Zeng
- , Shihan Liu
- & Lizhu Gao
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Chemoselectivity change in catalytic hydrogenolysis enabling urea-reduction to formamide/amine over more reactive carbonyl compounds
The selective transformation of a less reactive carbonyl moiety in the presence of more reactive ones can realize straightforward and environmentally benign chemical processes but such a transformation is highly challenging. Here, the authors report an Ir catalyst for the selective hydrogenolysis of urea derivatives, which are the least reactive carbonyl compounds, affording formamides and amines even in the presence of more reactive carbonyl groups such as ester.
- Takanori Iwasaki
- , Kazuki Tsuge
- & Kyoko Nozaki
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Integrating I(I)/I(III) catalysis in reaction cascade design enables the synthesis of gem-difluorinated tetralins from cyclobutanols
gem-Difluorinated motifs are prevalent in numerous leading pharmaceuticals. Here the authors merge I(I)/I(III)-catalysed fluorination and C(sp3)-F bond activation to generate these motifs directly from 1,3-diaryl cyclobutanols in a single operation.
- Joel Häfliger
- , Louise Ruyet
- & Ryan Gilmour
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Data-driven design of new chiral carboxylic acid for construction of indoles with C-central and C–N axial chirality via cobalt catalysis
The design of efficient and selective catalysts is a formidable challenge in chemical science. Here the authors design a data-driven workflow to achieve the digitalized knowledge transfer between the synthetically relevant transformations, which was demonstrated in the prediction of chiral carboxylic acid co-catalyst for the cobalt-catalyzed asymmetric C–H alkylation of indoles.
- Zi-Jing Zhang
- , Shu-Wen Li
- & Lutz Ackermann
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Computation-based regulation of excitonic effects in donor-acceptor covalent organic frameworks for enhanced photocatalysis
The donor-acceptor (D-A) interaction and exciton binding energy have been investigated for a series of D-A pairs by DFT calculations. Here, the authors synthesize the corresponding D-A COFs, and demonstrate that their photocatalytic hydrogen production activities match well with the calculation results.
- Yunyang Qian
- , Yulan Han
- & Hai-Long Jiang
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Retrosynthesis prediction using an end-to-end graph generative architecture for molecular graph editing
Retrosynthesis prediction is a fundamental problem in organic synthesis. Here, inspired by simplified arrow-pushing reaction mechanisms, the authors develop a graph-to-edits framework, Graph2Edits, based on graph neural network for retrosynthesis prediction.
- Weihe Zhong
- , Ziduo Yang
- & Calvin Yu-Chian Chen
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Article
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Single-step retrosynthesis prediction by leveraging commonly preserved substructures
Retrosynthesis is a critical task for organic chemistry with numerous industrial applications. Here, the authors build a machine learning model to learn the concept of substructures from a large reaction dataset to achieve chemist-like intuitions.
- Lei Fang
- , Junren Li
- & Jian-Guang Lou
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Article
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Smart thrombosis inhibitors without bleeding side effects via charge tunable ligand design
Treatments to prevent thrombosis are suboptimal. Here, the authors identify a lead an antithrombotic drug targeting polyphosphate based on switchable protonation states for the anion-binding groups, demonstrating antithrombotic activity in multiple mouse models, not causing bleeding, and well tolerated.
- Chanel C. La
- , Stephanie A. Smith
- & Jayachandran N. Kizhakkedathu
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Copper-catalyzed asymmetric C(sp2)–H arylation for the synthesis of P- and axially chiral phosphorus compounds
Although transition metal-catalyzed C–H bond functionalization is a widely used method in organic synthesis, many methods rely on metals of low abundance. Here, the authors report a copper-catalyzed, asymmetric C–H arylation using diaryliodonium salts.
- Shao-Bai Yan
- , Rui Wang
- & Wei-Liang Duan
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Copper(I)-catalyzed asymmetric alkylation of α-imino-esters
Asymmetric alkylation of enolates is an important method for the formation of α-stereogenic carbonyls but generally requires the introduction and then removal of chiral auxiliaries. Here, the authors report a copper-catalyzed asymmetric alkylation of α-amino esters.
- Zong-Ci Liu
- , Zi-Qing Wang
- & Liang Yin
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Electrosynthesis of polymer-grade ethylene via acetylene semihydrogenation over undercoordinated Cu nanodots
Cu-based catalysts for the conversion of C2H2 to C2H4 are plagued by side reactions. Here, Cu nanodots for C2H2 semihydrogenation are reported to reach current densities >400 mA cm−2 and selectively produce polymer-grade ethylene over 130 h.
- Weiqing Xue
- , Xinyan Liu
- & Jie Zeng
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Article
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An α-chloroaldehyde-based formal synthesis of eribulin
Eribulin is an anticancer drug and the most structurally complex non-peptidic drug made by chemical synthesis. Here, the authors report a streamlined synthesis of eribulin that creates new opportunities for drug discovery and development.
- Anissa Kaghad
- , Dimitrios Panagopoulos
- & Robert Britton
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Article
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Ring-closing C–O/C–O metathesis of ethers with primary aliphatic alcohols
Transetherifications between ethers and alcohols are fundamental organic reactions that are frequently used for the preparations of unsymmetrical ethers. In this article, the authors challenge the fundamental tenets of the traditional transetherification mechanism via systematic experimental and computational investigations of a Re2O7-mediated annulation.
- Hongmei Liu
- , Qing Huang
- & Youwei Xie
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Article
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Transition-metal-free silylboronate-mediated cross-couplings of organic fluorides with amines
C–N bond cross-coupling is fundamental in organic chemistry, but the readily available organic fluorides are unsuitable as coupling substrates. Here, we realize defluorinative cross-coupling with amines via a silylboronate-mediated strategy.
- Jun Zhou
- , Zhengyu Zhao
- & Norio Shibata
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3-sulfonyloxyaryl(mesityl)iodonium triflates as 1,2-benzdiyne precursors with activation via ortho-deprotonative elimination strategy
Preparation of functionalized analogues of 1,2-benzdiyne, from heavily substituted as well as benzofused scaffolds, is challenging. Here, the authors develop an array of 3-sulfonyloxyaryl(mesityl)iodonium triflates as 1,2-benzdiyne precursors, triggered from ortho-deprotonative elimination.
- Haoyin Yuan
- , Wenhao Yin
- & Yang Li
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Article
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Interfacial assembly of binary atomic metal-Nx sites for high-performance energy devices
An interfacial assembly strategy was developed to construct single-atom binary Fe/Co-Nx sites with a high accessible site density of 7.6 × 1019 sites per gram which results in increased power densities in fuel cells and Zn/air batteries.
- Zhe Jiang
- , Xuerui Liu
- & Jin-Song Hu
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A pyrolysis-free Ni/Fe bimetallic electrocatalyst for overall water splitting
A well-defined catalyst with dual Ni/Fe atomic active sites was created using a pyrolysis-free approach. The as-made catalyst was used for overall electrochemical water splitting in both acidic and alkaline electrolytes with low overpotentials.
- Ying Zang
- , Di-Qiu Lu
- & Shuang-Quan Zang
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Article
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Modular and practical diamination of allenes
Diamination of allenes with two different acyclic and cyclic alkyl amines remains a daunting challenge. Here, the authors report a modular and practical diamination of allenes, which offers efficient syntheses of β,γ-diamino carboxylates and sulfones.
- Jian-Jun Dai
- , Xianglin Yin
- & Mingji Dai
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Article
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Identification of tagged glycans with a protein nanopore
The structural complexity of glycans seriously challenges the currently available analytical methods. Here, the authors report the identification of glycan isomers, glycans with varying chain lengths, and distinct branched glycans, via a glycan derivatization strategy and nanopore sensing.
- Minmin Li
- , Yuting Xiong
- & Guangyan Qing
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Article
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Arene C–H borylation strategy enabled by a non-classical boron cluster-based electrophile
Electrophilic borylation of sterically hindered arenes is a challenging transformation. Here, authors report a metal-free electrophilic C–H borylation of hindered arenes using a boron cluster reagent producing valuable aryl boronic esters.
- Sangmin Kim
- , Joseph W. Treacy
- & Alexander M. Spokoyny
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Article
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Small molecule-nanobody conjugate induced proximity controls intracellular processes and modulates endogenous unligandable targets
Induced proximity can be used to control diverse cellular processes. Here, the authors develop nanobody-based proximity inducers called SNACIPs, which can be used to regulate either tagged or endogenous proteins, and demonstrate their use in blocking microtubule nucleation for tumour growth inhibition in vivo.
- Xiaofeng Sun
- , Chengjian Zhou
- & Xi Chen
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Article
| Open Access
One-pot synthesis of hyperbranched polymers via visible light regulated switchable catalysis
Switchable catalysis promises exceptional efficiency in synthesizing polymers with increasing structural complexity but current achievements in such attempts are limited to constructing linear block copolymers. Here the authors report a visible light regulated switchable catalytic system capable of synthesizing hyperbranched polymers in a one-pot/two-stage procedure with commercial glycidyl acrylate as a heterofunctional monomer.
- Shuaishuai Zhu
- , Maoji Zhao
- & Xiaolin Xie
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Article
| Open Access
Highly selective electrocatalytic alkynol semi-hydrogenation for continuous production of alkenols
Thermocatalytic alkynol semi-hydrogenation often uses high-pressure H2 and Pd-based catalysts. Here, using a Cu-based electrode, the authors investigate the electrocatalytic alkynol semi-hydrogenation to alkenols with water as the hydrogen source.
- Jun Bu
- , Siyu Chang
- & Jian Zhang
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Article
| Open Access
Li3TiCl6 as ionic conductive and compressible positive electrode active material for all-solid-state lithium-based batteries
An ideal positive electrode for all-solid-state Li batteries should be ionic conductive and compressible. However, this is not possible with state-of-the-art metal oxides. Here, the authors demonstrate the use of an ionic conductive metal chloride as compressible positive electrode active material.
- Kai Wang
- , Zhenqi Gu
- & Cheng Ma
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Article
| Open Access
Cobalt-catalyzed enantioselective intramolecular reductive cyclization via electrochemistry
1,6 enynes are a useful synthetic building block, but their use asymmetric intramolecular reductive couplings with cobalt catalysts have not been well-explored. Here, the authors describe an enantioselective intramolecular reductive coupling of enynes via the combination of electrochemistry and cobalt catalysis.
- Shiquan Gao
- , Chen Wang
- & Junliang Zhang
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Article
| Open Access
On-surface synthesis of enetriynes
Enetriynes, which belong to the enyne family, are characterized by a distinct electron-rich carbon-bonding scheme. Here, the authors report the formation of enetriynes with high selectivity by tetramerization of terminal alkynes on Ag(100).
- Nan Cao
- , Biao Yang
- & Johannes V. Barth
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Article
| Open Access
Ex-situ generation and synthetic utilization of bare trifluoromethyl anion in flow via rapid biphasic mixing
The trifluoromethyl anion rapidly decomposes into difluorocarbene (:CF2) and fluorine ion, limiting its applicability in synthesis. Here, the authors report a strategy to generate and use the short-lived CF3- intermediate from stable CF3H gas via fast biphasic mixing in precisely customized flow dissolvers.
- Hyune-Jea Lee
- , Jeong-Un Joo
- & Heejin Kim
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Article
| Open Access
Non-covalent ligand-oxide interaction promotes oxygen evolution
If and how non-bonding ligands mediate the electronic states of metal sites is interesting yet remains to be explored. Here the authors show that a non-covalent phenanthroline can promote the population of Co4+ and induce polaron-like Co sites for improved water oxidation.
- Qianbao Wu
- , Junwu Liang
- & Chunhua Cui
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Article
| Open Access
Synthesis of precisely functionalizable curved nanographenes via graphitization-induced regioselective chlorination in a mechanochemical Scholl Reaction
The synthesis of functionalizable nanographenes remains challenging. Here, the authors report that mechanochemical Scholl reaction allows access to regioselectively modifiable curved nanographenes in a high-yielding and general manner.
- Jovana Stanojkovic
- , Ronny William
- & Mihaiela C. Stuparu
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Article
| Open Access
Interfacial solute flux promotes emulsification at the water|oil interface
Emulsions are critical across a broad spectrum of industries. Here authors demonstrate a mechanism of spontaneous droplet formation, where the interfacial solute flux promotes droplet formation at the liquid-liquid interface when a phase transfer agent is present.
- Guillermo S. Colón-Quintana
- , Thomas B. Clarke
- & Jeffrey E. Dick
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Article
| Open Access
Dearomative triple elementalization of quinolines driven by visible light
Organoboron and organosilicon compounds have potential applications in various fields including materials science and medicinal chemistry. Here the authors report a protocol that enables the dearomative carbo-sila-boration of quinolines.
- Shiho Ishigaki
- , Yuki Nagashima
- & Ken Tanaka
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Article
| Open Access
Rational design of N-heterocyclic compound classes via regenerative cyclization of diamines
Introducing unknown compound classes is the key to extent the chemical space qualitatively. Here the authors report on a concept to design heterocyclic compound classes rationally and the synthesis of unknown classes of N-heterocyclic compounds
- Robin Fertig
- , Felix Leowsky-Künstler
- & Rhett Kempe
Chemoenzymatic synthesis of genetically-encoded multivalent liquid N-glycan arraysBrowse broader subjects
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