Chemical synthesis articles within Nature Communications

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  • Article
    | Open Access

    A limitation of robotic platforms in chemistry is the lack of feedback loops to adjust the conditions in-operando. Here the authors present a dynamically programmable robotic system that uses sensors for real-time adaptation, achieving yield improvements in syntheses and discovering new molecules.

    • Artem I. Leonov
    • , Alexander J. S. Hammer
    •  & Leroy Cronin

  • Article
    | Open Access

    Macrolactones exhibit distinct conformational and configurational properties and are widely found in natural products but catalysts to govern both macrolactone formation and stereochemical control remain largely unexplored. Here, the authors disclose an N-heterocyclic carbene (NHC)-catalyzed enantioselective synthesis of chiral macrolactones varying in ring size from sixteen to twenty members that feature distinct configurationally stable planar stereogenicity.

    • Xiaokang Lv
    • , Fen Su
    •  & Yonggui Robin Chi

  • Article
    | Open Access

    Nature generates the stereoisomeric yohimbine alkaloids using bioavailable monoterpene secolaganin as the building block. Here, the authors reset the stage by the development of a bioinspired coupling, in which the pentacyclic skeleton is constructed through enantioselective kinetic resolution of an achiral, easily accessible synthetic surrogate.

    • Meiyi Tang
    • , Haigen Lu
    •  & Liansuo Zu

  • Article
    | Open Access

    While the reported methods for the synthesis of organoselenium compounds mainly employ preformed activated selenium reagents, the direct utilization of elemental selenium in the synthesis is a more attractive but challenging strategy. Here, the authors report the rapid synthesis of versatile organoselenium compounds via mechanical stimulation.

    • Shanshan Chen
    • , Chunying Fan
    •  & Xiaofeng Wei

  • Article
    | Open Access

    Direct and site-selective C–H functionalization of alkenes under environmentally benign conditions represents a useful and attractive yet challenging transformation to access value-added molecules. Here, the authors report a protocol for a variety of intermolecular Heck-type functionalization of C(sp2)–H bond of alkenes by thianthrenation.

    • Ming-Shang Liu
    • , Hai-Wu Du
    •  & Wei Shu

  • Article
    | Open Access

    Regioselectivity prediction for many reactions remains a challenging target for a priori prediction. Here, the authors develop a machine learning model that predicts the outcomes of Minisci reactions.

    • Emma King-Smith
    • , Felix A. Faber
    •  & Alpha A. Lee

  • Article
    | Open Access

    The synthesis of molecular knots remains challenging. Here, the authors report the synthesis of a chiral molecular trefoil metallaknot by self-assembly which contains only 54 atoms in the backbone.

    • Zhiwen Li
    • , Jingjing Zhang
    •  & Richard J. Puddephatt

  • Article
    | Open Access

    Predicting the structure of lithium halide solid-state electrolytes from their composition alone is a challenge. Here, the authors introduce the “cationic polarization factor” that captures the key interactions of halide-based solid-state electrolytes and predicts the stacking structures.

    • Xiaona Li
    • , Jung Tae Kim
    •  & Xueliang Sun

  • Article
    | Open Access

    Directing group strategies have been used extensively in C–H activation reactions but current methods rely heavily on coordination with nitrogen or oxygen atoms in molecules and have therefore been found to exhibit limited generality in asymmetric syntheses. Here, the authors report enantioselective C–H activation with unsaturated hydrocarbons directed by phosphorus centres to rapidly construct libraries of axially chiral phosphines through dynamic kinetic resolution.

    • Zexian Li
    • , Minyan Wang
    •  & Zhuangzhi Shi

  • Article
    | Open Access

    Minor changes to complex structures can exert major influences on synthesis strategy and functional properties but synthetic difficulties can obstruct the exploration of natural product function. Here the authors explore two parallel series of picrotoxinin analogs and identify leads with selectivity between mammalian and insect ion channels.

    • Guanghu Tong
    • , Samantha Griffin
    •  & Ryan A. Shenvi

  • Article
    | Open Access

    As sulfonyl fluorides have found wide applications, synthetic access to β-hydroxy sulfonyl fluorides is desirable. Here, the authors report an electroreductive strategy for radical hydroxyl fluorosulfonylation of alkenes with sulfuryl chlorofluoride and molecular oxygen from air.

    • Qingyuan Feng
    • , Tianyu He
    •  & Shenlin Huang

  • Article
    | Open Access

    Peptide drug manufacturing commonly uses large amounts of hazardous solvents primarily due to multiple washings after each step. Here, the authors introduce the concept of a completely wash-free methodology that enables up to 95% waste reduction.

    • Jonathan M. Collins
    • , Sandeep K. Singh
    •  & Christopher L. Houser

  • Article
    | Open Access

    Here the authors demonstate that counter to expectation provided by the relevant standard reduction potentials, a chloroberyllate, [{SiNDipp}BeClLi]2, reacts with the group 1 elements (M = Na, K, Rb, Cs) to provide the respective heavier alkali metal analogues, [{SiNDipp}BeClM]2.

    • Kyle G. Pearce
    • , Han-Ying Liu
    •  & Michael S. Hill

  • Article
    | Open Access

    While heat modification is ubiquitous in biologic systems, it remains a significant challenge in artificial systems. Here the authors demonstrate thermal regulation of conversion between different rigid macrocycle atropisomers and related self-assemblies.

    • Jiaqi Liang
    • , Shuai Lu
    •  & Han-Yuan Gong

  • Article
    | Open Access

    Perfluorinated covalent triazine frameworks are promising proton-conducting materials with high content of phosphoric acid anchor sites to enhance proton conductivity but their synthesis is challenging. Here, the authors report a mild method to produce perfluorinated covalent triazine frameworks displaying high proton conductivity.

    • Lijiang Guan
    • , Zhaoqi Guo
    •  & Shangbin Jin

  • Article
    | Open Access

    [6,6]-Phenyl-C61-butyric acid methyl ester (PCBM), a star molecule in the fullerene field, has found wide applications in materials science. Here, the authors demonstrate the synthesis of buckyballs with fused-ring systems via electrosynthesis through radical α-C−H functionalization of the side-chain ester for both PCBM and its analogue.

    • Wei-Feng Wang
    • , Kai-Qing Liu
    •  & Guan-Wu Wang

  • Article
    | Open Access

    Pentavalent stereocentres encode an expanded stereochemical space, but their catalytic tractability remained unprecedented. In this report, the authors report that catalyst control over pentavalent stereocentres is feasible.

    • Anton Budeev
    • , Jianyang Dong
    •  & Christof Sparr

  • Article
    | Open Access

    Visible light-induced glycosylation reactions are achieved by either photoactivating a photosensitizer or using a stoichiometric activator, while glycosylation via a photoactive glycosyl donor was so far not reported. In this study, the authors develop a photosensitizer free visible-light-mediated glycosylation approach using photoactive 2-glycosyloxy tropone as the donor, obtaining a wide range of O-glycosides or oligosaccharides.

    • Jing Zhang
    • , Zhao-Xiang Luo
    •  & De-Cai Xiong

  • Article
    | Open Access

    The design of highly permeable polyamide (PA) membrane capable of precise ionic sieving remains challenging. Here, the authors report an anhydrous interfacial polymerization on the solid-liquid interface to eliminate water-caused side reactions, leading to a PA layer with an ionic sieving accuracy of 0.5 Å.

    • Guangjin Zhao
    • , Haiqi Gao
    •  & Hong Meng

  • Article
    | Open Access

    Solid-phase synthesis strategy is promising for fabricating desired complex metal nanoparticles on supports. Here, the authors synthesize CoFe@FeOx core-shell nanoparticles as the separator coatings via precise solid-phase method which effectively regulates polysulfides for lithium/ sodium-sulfur batteries.

    • Yanping Chen
    • , Yu Yao
    •  & Jian Liu

  • Article
    | Open Access

    γ-Amino acids and peptides analogues are common constituents of building blocks for numerous biologically active molecules, pharmaceuticals, and natural products. Here, the authors developed a multicomponent carbonylation technology that combines readily available amides, alkenes, and the feedstock gas carbon monoxide to build γ-amino acid derivatives in a single step.

    • Le-Cheng Wang
    • , Yang Yuan
    •  & Xiao-Feng Wu

  • Article
    | Open Access

    The use of heteroatom-centered anions as super-electron-donors (SEDs) for direct single-electron-transfer reactions has rarely been studied. Here, the authors show that heteroatom anions can be applied as SEDs to initiate radical reactions for synthesis of 3-substituted benzofurans, which have applications in both organic synthesis and pesticide development.

    • Shichun Jiang
    • , Wei Wang
    •  & Yonggui Robin Chi

  • Article
    | Open Access

    The discovery of highly enantioselective catalysts is challenging due to the complex multidimensional chemical space of asymmetric catalysis and inefficient screening methods. Here, the authors report a general strategy for ultra-high-throughput mapping of the chemical space of asymmetric catalysis with a combination of ion mobility-mass spectrometry and a diastereoisomerization strategy and identify enantioselective primary amine organocatalysts using this method.

    • Wenjing Nie
    • , Qiongqiong Wan
    •  & Suming Chen

  • Article
    | Open Access

    Sp2 carbon nucleophiles are generally not considered for transition metal-catalyzed asymmetric hydrofunctionalizations of unsaturated bonds due to challenges in cleaving corresponding inert sp2 C-H bonds. Here, the authors report a protocol to achieve asymmetric formal sp2 hydrocarbonations, including hydroalkenylation, hydroallenylation and hydroketenimination of both 1,3-dienes and alkynes via hydroalkylation and Wittig reaction cascade

    • Ming-Qiao Tang
    • , Zi-Jiang Yang
    •  & Zhi-Tao He

  • Article
    | Open Access

    The development of robust catalysts that could work under industrial-scale current densities bring promise but also a challenge for hydrogen production. Here, the authors report an in situ activation method to produce ferromagnetic ruthenium clusters that can catalyze the hydrogen evolution reaction at high current densities.

    • Jun Qi
    • , Yadong Du
    •  & Jieshan Qiu

  • Article
    | Open Access

    Polymersomes, as analogues of liposomes, have interesting physical and chemical properties, but have not yet been translated into clinical or industrial applications. Here, the authors report the development of a continuous flow process for the production of polymersomes at scale.

    • Chin Ken Wong
    • , Rebecca Y. Lai
    •  & Martina H. Stenzel

  • Article
    | Open Access

    The nucleophilic substitution reaction (SN2) is one of the oldest yet very useful organic transformations, but surprisingly, the nucleophilic character of isocyanides has never been explored in SN2 reactions. Here the authors show that isocyanides react as versatile nucleophiles in SN2 reactions with alkyl halides in a general manner to afford highly substituted secondary amides by in situ hydrolysis of the intermediate nitrilium ion.

    • Pravin Patil
    • , Qiang Zheng
    •  & Alexander Dömling

  • Article
    | Open Access

    The 1,2 migration reaction on tetracoordinate boron species have been well investigated but less work looked on 1,2-boryl radical shift for the construction of organoborons. Here, the authors demonstrate a visible-light-induced photoredox neutral decarboxylative radical cross-coupling reaction, which undergoes a radical 1,2-boron shift to give a translocated C-radical for further capture of versatile radical acceptors

    • Yu Guo
    • , Xiaosha Wang
    •  & Qiuling Song

  • Article
    | Open Access

    The Mannich reaction is a well-established method for the synthesis of β-amino carbonyl compounds while the analogous reactions of homo-enol or its equivalents with imines or iminium ions are much less explored. Here, the authors describe a homo-Mannich reaction of cyclopropanol with imines generated via a Bischler-Napieralski reaction.

    • Hanyue Qiu
    • , Xinghai Fei
    •  & Min Zhang

  • Article
    | Open Access

    The introduction of metal sites into polyoxometalates is key for tuning their structure and reactivity but the complex mechanisms which govern metal functionalization of polyoxometalates are still poorly understood. Here, the authors report a coupled set of light-dependent and light-independent reaction equilibria controlling the mono- and di- metal-functionalization of a prototype molecular vanadium oxide cluster

    • Stefan Repp
    • , Moritz Remmers
    •  & Carsten Streb

  • Article
    | Open Access

    Silicon-stereogenic optically active silylboranes could potentially allow the formation of chiral silyl nucleophiles as well as the synthesis of various chiral silicon compounds but the synthesis of such silicon-stereogenic silylboranes remains underdeveloped. Here, the authors report the synthesis of silicon-stereogenic optically active silylboranes via a stereospecific Si–H borylation of chiral hydrosilanes in high yield enantiospecificity

    • Xihong Wang
    • , Chi Feng
    •  & Hajime Ito

  • Article
    | Open Access

    Achieving stable and selective chlorine production is of high interest yet challenging. Here the authors report an amorphous CoOxCly catalyst prepared by in situ electrodeposition in acidic saline electrolyte which shows ~100% chlorine evolution selectivity with low overpotential and high stability over 500 h.

    • Mengjun Xiao
    • , Qianbao Wu
    •  & Chunhua Cui

  • Article
    | Open Access

    During solid-phase peptide synthesis (SPPS) inherent side reactions of the protected amino acids such as α-C racemization generate by-products that are hard to remove. Here, the authors report thiol-labile amino protecting group for SPPS, DNPBS group, which suppresses the main side reactions observed during conventional SPPS.

    • Yifei Zhou
    • , Hongjun Li
    •  & Chuanzheng Zhou

  • Article
    | Open Access

    Cellular glycosylation is complex and heterogeneous, which is challenging to reproduce synthetically. Here, the authors report on enzymatic remodelling of multivalent glycosylated bacteriophages to produce genetically encoded library of N-glycans which can be used to measure glycan-protein interactions with lectins on the surface of live cells and organs.

    • Chih-Lan Lin
    • , Mirat Sojitra
    •  & Ratmir Derda

  • Article
    | Open Access

    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

  • Article
    | Open Access

    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

  • Article
    | Open Access

    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

  • Article
    | Open Access

    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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