Chemical synthesis articles within Nature Communications

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  • Article
    | Open Access

    Transition metal-catalysed C–H hydroxylation is one of the most notable synthetic advances to access alcohols and phenols. Here, the authors report a metal-free, mild C–H hydroxylation of (hetero)arenes via boron-mediated chelation.

    • Jiahang Lv
    • , Binlin Zhao
    •  & Zhuangzhi Shi

  • Article
    | Open Access

    Controlling the partial reduction of quinolines is challenging, given the competing overreduction to tetrahydroquinolines. Here, the authors report a cobalt-amido cooperative catalyst for the selective, partial transfer hydrogenation of quinolines to 1,2-dihydroquinolines with H3N·BH3 as reductant.

    • Maofu Pang
    • , Jia-Yi Chen
    •  & Wenguang Wang

  • Article
    | Open Access

    Incorporation of supramolecular macrocycles into porous organic polymers can increase uptake of guest molecules through host−guest interactions. Here the authors report a pillar[5]quinone derived multi-microporous organic polymer, which show a superior performance in radioactive iodomethane capture and storage.

    • Kecheng Jie
    • , Yujuan Zhou
    •  & Sheng Dai

  • Article
    | Open Access

    Many reagents have been developed for cysteine-specific protein modification. However, few of them allow for multi-functionalization of a single Cys residue and disulfide bridging bioconjugation. Here the authors report 3-bromo-5-methylene pyrrolones as a simple, robust and versatile class of reagents for cysteine-specific protein modification.

    • Yingqian Zhang
    • , Chuanlong Zang
    •  & Chuanzheng Zhou

  • Article
    | Open Access

    Aspartimide formation is a frequently occurring problem during peptide synthesis. Here, the authors present cyanosulfurylides as a protection group that masks aspartic acid residues during solid phase peptide synthesis, thus preventing aspartimide formation, and can be removed with N-chlorosuccinimide.

    • Kevin Neumann
    • , Jakob Farnung
    •  & Jeffrey W. Bode

  • Article
    | Open Access

    The development of thia-Baeyer-Villiger reactions has been elusive so far due to competitive oxidation of sulfoxides to sulfones. Here, the authors show a thia-Baeyer-Villiger-type oxidations converting dibenzothiophene derivatives into sulfinic esters with t-BuOOH and an iron catalyst under UV irradiation.

    • Xiaofeng Ma
    • , Yazhou Liu
    •  & István E. Markó

  • Article
    | Open Access

    Asymmetric intermolecular hydroamination of alkenes is a challenging process, potentially leading to useful chiral amines. Here, the authors report unsymmetric NNN tridentate ligands promoting the cobalt-catalyzed radical hydroamination of alkenes via hydrogen atom transfer, also in an asymmetric fashion.

    • Xuzhong Shen
    • , Xu Chen
    •  & Zhan Lu

  • Comment
    | Open Access

    While electrosynthesis represents a green and advantageous alternative to traditional synthetic methods, electrochemical reactions still suffer from some drawbacks that require further efforts in order to fully express the potential of electricity-driven transformations. In this Comment, we will briefly discuss both the advantages and limitations of electrosynthesis, especially when compared with the other traditional synthetic organic methods, and share some forward-looking thoughts on the future developments of electrochemical reactions.

    • Yong Yuan
    •  & Aiwen Lei

  • Comment
    | Open Access

    A pharmaceutical industry viewpoint on how the fundamental laws of photochemistry are used to identify the parameters required to implement photochemistry from lab to scale. Parameters such as photon stoichiometry and light intensity are highlighted within to inform future publications.

    • Holly E. Bonfield
    • , Thomas Knauber
    •  & Lee J. Edwards

  • Article
    | Open Access

    Trifluoromethyl ethers are important bioactive targets in pharmaceuticals and agrochemicals, however, their synthesis is often not straightforward. Here, the authors disclose a reagent for the nucleophilic trifluoromethoxylation of alkyl halides without silver and under mild conditions.

    • Yan Li
    • , Yang Yang
    •  & Pingping Tang

  • Article
    | Open Access

    Small non-polymeric molecules have tremendous structural diversity that can be used to represent information. Here the authors encode data in synthesized libraries of Ugi products.

    • Christopher E. Arcadia
    • , Eamonn Kennedy
    •  & Jacob K. Rosenstein

  • Article
    | Open Access

    Heterocycles containing difluoromethyl groups are molecules with potential application in pharmaceutical, agricultural and materials science. Here, the authors show an organophotocatalytic difluoromethylation of heterocycles using O2 as green oxidant and preliminarily study the products’ bioactivity.

    • Wei Zhang
    • , Xin-Xin Xiang
    •  & Xin Li

  • Article
    | Open Access

    Meroterpenes are a particularly important class of biologically active bicyclo[3.3.1]nonane-containing molecules. Here, the authors report a general strategy toward these valuable targets based on abiotic annulation/rearrangement steps resulting in a concise total synthesis of garsubellin A.

    • Xingyu Shen
    • , Chi P. Ting
    •  & Thomas J. Maimone

  • Article
    | Open Access

    Bio‐based compounds often suffer from high production cost and low performance when used to synthesise macromolecules. Here the authors show the conversion of (+)‐3‐ carene, a by‐product of the cellulose industry, into its ε‐lactams and then to polyamides with high‐performance thermal properties.

    • Paul N. Stockmann
    • , Daniel Van Opdenbosch
    •  & Volker Sieber

  • Article
    | Open Access

    Fluorinated or fluoroalkylated allenes are versatile building blocks for medicinal and material chemistry. Here, the authors show a regioselective trifunctionalization of 1,3-enynes proceeding through double C-F bond formation and concomitant installation of a -NSO2Ph group to the allene moiety.

    • Munira Taj Muhammad
    • , Yihang Jiao
    •  & Hongli Bao

  • Article
    | Open Access

    The assembly of giant silver clusters by using macrocylic multidentate ligand remains a challenge. Here, the authors synthesize a chromate-templated 88-nuclei silver super calix and reveal the role of anion templating effects and a hierarchical assembly mechanism.

    • Zhi Wang
    • , Hai-Feng Su
    •  & Lan-Sun Zheng

  • Article
    | Open Access

    Alternative carbene precursors for metal-catalyzed cross coupling may expand the portfolio of methods for C-C bond construction. Here, the authors report a Suzuki−Miyaura coupling of Pd−carbene complexes formed by desulfurization of thioureas or thioamides and affording a broad array of amidinium salts and diaryl ketones.

    • Shaoyu Mai
    • , Wendong Li
    •  & Qiuling Song

  • Article
    | Open Access

    CO2 conversion into value-added chemicals is a promising strategy to exploit renewable feedstocks. Here, the authors report the iridium-catalysed synthesis of higher carboxylic acids from ethers, CO2 and H2.

    • Ying Wang
    • , Qingli Qian
    •  & Buxing Han

  • Article
    | Open Access

    Photoresponsive polymers are receiving great attention due to the increasing demands on smart optical and biological materials. Here, the authors report a C–H-activated polyspiroannulation route to in situ generate photoresponsive spiro-polymers with potential applications in photopatterning and silicon photonics techniques.

    • Ting Han
    • , Zhanshi Yao
    •  & Ben Zhong Tang

  • Article
    | Open Access

    Synthetic labs rely on a vast number of chemicals, which are often unstable with time and affected by price fluctuations. Here, the authors report ad hoc developed cartridge reactionware for the synthesis of four different targets in a time- and cost-saving manner.

    • Sergey S. Zalesskiy
    • , Philip J. Kitson
    •  & Leroy Cronin

  • Article
    | Open Access

    The dehydrogenative C-H/N-H cross-coupling serves to install nitrogen functionalities into arenes with the highest atom economy. Here, the authors report an electrochemical cross-coupling between aromatics and sulfonimides through an N-radical addition pathway under oxidant- and catalyst-free conditions.

    • Xia Hu
    • , Guoting Zhang
    •  & Aiwen Lei

  • Article
    | Open Access

    Difluorocarbene is a versatile and efficient intermediate for fluorine incorporation. Here, the authors show that difluorocarbene can be oxidized to carbonyl fluoride and this process is confirmed in 18O-trifluoromethoxylation reactions, by observation of AgOCF3 species and theory.

    • Jiao Yu
    • , Jin-Hong Lin
    •  & Ji-Chang Xiao

  • Article
    | Open Access

    Chiral 3-azetidinones are structural analogues of medicinally relevant β-lactams, however their synthesis and reactivity are underexplored. Here, the authors show a highly enantioselective copper-catalyzed [3 + 1]-cycloaddition generating 2-azetidines, which react with nucleophiles yielding amino acids via 3-azetidinones.

    • Kostiantyn O. Marichev
    • , Kuiyong Dong
    •  & Michael P. Doyle

  • Article
    | Open Access

    Extending the π‐conjugation of phthalocyanine dyes, while synthetically challenging, has the potential to produce desirable new molecular materials. Here, the authors use a templated on‐surface approach to synthesize several extended phthalocyanine derivatives from the same building block, including a lanthanide superphthalocyanine and an open‐chain polycyanine.

    • Qitang Fan
    • , Jan-Niclas Luy
    •  & J. Michael Gottfried

  • Article
    | Open Access

    Methods to prepare 1,2-diamines are desirable due the importance of these compounds as drug scaffolds and organic ligands for metals. Here, the authors report an electrochemical metal-free 1,2- diamination of aryl alkenes with sulfamides to 1,2-diamines with excellent diastereoselectivity.

    • Chen-Yan Cai
    • , Xiao-Min Shu
    •  & Hai-Chao Xu

  • Article
    | Open Access

    Incorporating mesopores and active sites into metal-organic framework materials has proven advantageous for their catalytic application, but remains challenging to achieve. Here the authors obtain mesoporous, defect-rich metal-organic frameworks through templated electrosynthesis using ionic liquids as both electrolyte and template.

    • Xinchen Kang
    • , Kai Lyu
    •  & Martin Schröder

  • Article
    | Open Access

    Fluorescent supramolecular coordination complexes are of interest for chemical sensing and optical devices. Here the authors synthesize nine organoplatinum metallacycles with high quantum yields, whose fluorescence wavelengths are tuned through manipulation of their photoinduced electron transfer and intramolecular charge transfer properties.

    • Jun-Long Zhu
    • , Lin Xu
    •  & Hai-Bo Yang

  • Article
    | Open Access

    Derivatization of natural products is a powerful approach to generate new molecules for biological screenings. Here, the authors employ C-H oxidation and ring expansion methods for the preparation of a library of medium-sized ring skeleta, which occupy a unique chemical space based on chemoinformatic analysis.

    • Changgui Zhao
    • , Zhengqing Ye
    •  & Weiping Tang

  • Article
    | Open Access

    In this paper, the authors introduce a structurally elegant 2D triquinoline molecule as a discrete model for graphitic materials with atom-sized voids. The compound has unusual chemical properties, including high proton affinity and rich supramolecular behavior, forming complexes via both π-π and CH-π contact modes.

    • Shinya Adachi
    • , Masakatsu Shibasaki
    •  & Naoya Kumagai

  • Article
    | Open Access

    Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues contamination. Here the authors show a fluorinated alcohol based catalytic system for polypeptide synthesis from α-amino acid N-carboxyanhydride, fulfilling cocatalyst and metal free conditions with high rate and selectivity.

    • Wei Zhao
    • , Yanfeng Lv
    •  & Nikos Hadjichristidis

  • Article
    | Open Access

    Palladium-catalyzed late-stage diversification of structurally complex peptides has major shortcomings. Here, the authors developed a ruthenium-catalyzed C–H alkylations of peptides allowing for fluorescence labeling, late-stage diversifications and peptide ligations by solid phase peptide synthesis.

    • Alexandra Schischko
    • , Nikolaos Kaplaneris
    •  & Lutz Ackermann

  • Article
    | Open Access

    Dialkyl biaryl phosphines find wide application in catalysis as ligands. Here, the authors report a rhodium-catalysed hydroarylation of alkenes and alkynes with tertiary phosphines through P(III)-chelation assisted C-H activation affording a library of functionalized phosphines which hold potential in catalytic applications.

    • Dingyi Wang
    • , Ben Dong
    •  & Zhuangzhi Shi

  • Article
    | Open Access

    Unprotected carboxylic acids are classically deemed to be unsusceptible to conjugated additions due to acid-base neutralization. Here, the authors show that the use of an appropriate Lewis acid allows the catalytic addition of organometallics to unprotected carboxylic acids, also in an asymmetric fashion.

    • Xingchen Yan
    •  & Syuzanna R. Harutyunyan

  • Article
    | Open Access

    C19 hydroxylation is a unique feature of some bioactive steroids. Here, the authors developed a direct C19 hydroxylation approach to scalably access 19-OH-cortexolone in the host T. cucumeris and then converted the product into various pharmaceutically useful products via chemical synthesis.

    • Junlin Wang
    • , Yanan Zhang
    •  & Qianghui Zhou

  • Article
    | Open Access

    Chemically synthesized graphene nanosheets offer device design flexibility and improved optoelectronic performance. Here, the authors report solution-processed distributed feedback lasers with graphene nanosheets as active media having linewidths < 0.13 nm, long operational lifetimes and low thresholds.

    • Víctor Bonal
    • , Rafael Muñoz-Mármol
    •  & María A. Díaz-García

  • Article
    | Open Access

    Bottom-up synthesis from rationally designed precursor molecules is one of the most promising routes to single-walled carbon nanotubes of any desired chirality. Here, the authors present a combinatorial approach to easily assemble a variety of these complex nanotube precursors from simple complementary segments.

    • Joerg Tomada
    • , Thomas Dienel
    •  & Konstantin Amsharov

  • Article
    | Open Access

    Molecular bilayer graphene — a discrete assembly of two stacked graphene fragments — is challenging to produce in pure form. Here, the authors are able to synthesize and characterize stable molecular bilayer graphenes by the π−π stacking of two identical, well-defined nanographene sheets.

    • Xin-Jing Zhao
    • , Hao Hou
    •  & Yuan-Zhi Tan

  • Article
    | Open Access

    While photoredox catalysis provides organic chemistry new avenues for chemical reactions, typical photocatalysts require expensive noble metals and show modest stabilities. Here, authors examine lead halide perovskites nanocrystals as stable and tunable photoredox catalysts for organic synthesis.

    • Xiaolin Zhu
    • , Yixiong Lin
    •  & Yong Yan

  • Article
    | Open Access

    Catalytic transformations involving main group compounds is much less developed than carbon chemistry. Here, the authors report the use of catalytic or stoichiometric tBuOK in presence of a hydrogen acceptor for efficient P–P and P–heteroatom coupling reactions.

    • Lipeng Wu
    • , Vincent T. Annibale
    •  & Ian Manners

  • Article
    | Open Access

    Inverse electron-demand cycloadditions in palladium catalysis are inherently limited by the linear selectivity in the allylic substitution step. To overcome this issue, the authors report a synergetic iridium (branched-selective) and amine catalysis in [4+2] cycloadditions of vinyl aminoalcohols with carbonyls.

    • Mao-Mao Zhang
    • , Ya-Ni Wang
    •  & Wen-Jing Xiao

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