Organic chemistry articles within Nature Communications

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  • Article
    | Open Access

    Long-standing radical species have raised noteworthy concerns in organic chemistry and but there remains a substantial challenge to produce long-standing radicals by light. Here, the authors demonstrate a stable dithienylethene derived photochromic radical for detection of peroxides and ozone.

    • Xuanying Chen
    • , Wandong Zhao
    •  & Liangliang Zhu

  • 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

    Can organic chemistry mimic nature in efficiency and sustainability? Not yet, but recent developments in photoredox catalysis animated the synthetic chemistry field, providing greener opportunities for industry and academia.

    • Giacomo E. M. Crisenza
    •  & Paolo Melchiorre

  • 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

    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

    Sonogashira cross-coupling is a powerful strategy to prepare functionalized internal alkynes. Here, the authors report a domino sequence for the generation of γ-/δ-alkynyl nitriles and γ-alkynyl ketones from the coupling of terminal alkynes with O-acyloximes derived from cycloalkanones and acylic ketones, respectively.

    • Zhaodong Li
    • , Rubén O. Torres-Ochoa
    •  & Jieping Zhu

  • Article
    | Open Access

    In contrast to the well-established palladium-catalyzed version, the nickel-catalyzed carbonylative coupling is underdeveloped. Here the authors report a nickel-catalyzed allylic carbonylative coupling with alkyl zinc reagents, allowing for preparation of β,γ-unsaturated ketones in a linear-selective fashion.

    • Yangyang Weng
    • , Chenhuan Zhang
    •  & Yifeng Chen

  • 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

    Structural diversity of organic fluorophores is of importance for several applications (fluorescent markers, photosensitizers, etc.). Here the authors report a method to merge radical chemistry with C–H activation to construct a brand-new class of flavylium fluorophores starting from (hetero)aryl ketones and alkynes.

    • Jiangliang Yin
    • , Yuming Zhang
    •  & Jingsong You

  • Article
    | Open Access

    Organic semiconductors are considered promising Surface Enhanced Raman Spectroscopy platforms. Here the authors demonstrate that metal-free films based on a π-conjugated molecule containing a fully π-conjugated backbone provides an enhancement factor of 105 and detection limit of 10−9 M for methylene blue.

    • Gokhan Demirel
    • , Rebecca L. M. Gieseking
    •  & Hakan Usta

  • Article
    | Open Access

    Covalently bridged π-stacked dimers are excellent molecular platforms for understanding the relationship between stacking orientation and properties. Here, the authors synthesize a pair of π-stacked dimers that are aligned either cofacially or crosswise, allowing them to compare how the intramolecular stacking mode affects each dimer’s photoswitching properties.

    • Ru-Qiang Lu
    • , Xiao-Yun Yan
    •  & Xiao-Yu Cao

  • Article
    | Open Access

    Despite their higher abundance, 3d metal-based catalysts are less investigated than their precious metal counterparts. Here, the authors report a cobalt-triphos complex as molecularly-defined non-noble metal catalyst for the reductive amination of carbonyl compounds with gaseous ammonia and hydrogen.

    • Kathiravan Murugesan
    • , Zhihong Wei
    •  & Rajenahally V. Jagadeesh

  • 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

    Nucleophiles cannot be directly reacted with enolates due to polarity mismatching. Here, the authors developed an umpolung strategy for the selective synthesis of α-alkoxy carbonyl compounds by reaction of iridium enolates with nucleophilic alcohols promoted by an iodine(III) reagent.

    • Amparo Sanz-Marco
    • , Samuel Martinez-Erro
    •  & Belén Martín-Matute

  • Article
    | Open Access

    Enantiodivergent methods, which to access both enantiomers of the same compound, are of importance in drug synthesis. Here, the authors show that by simply changing a NiBu- to a NMe-group in readily available amine organocatalysts, high stereocontrol and broad scope are achieved in eight asymmetric reactions.

    • Jun Dai
    • , Zhuang Wang
    •  & Zhihui Shao

  • Article
    | Open Access

    Purely organic ultralong room temperature phosphorescence (URTP) attracts attention but high efficiencies are rarely achieved. Here the authors use ultrafast spectroscopy to investigate a system of 1,8-naphthalic anhydride in organic hosts and reveal that a cluster exciton forms as a transient state before the guest acts as an energy trap for the URTP state.

    • Xuepeng Zhang
    • , Lili Du
    •  & Ben Zhong Tang

  • Article
    | Open Access

    The Aza Paternò-Büchi reaction is arguably among the most direct approaches to functionalized azetidines, which are common medicinal scaffolds. Here, the authors report a mild and selective visible light-enabled intramolecular aza Paternò-Büchi reaction yielding bicyclic azetidines in high yields and diastereoselectivity.

    • Marc R. Becker
    • , Alistair D. Richardson
    •  & Corinna S. Schindler

  • Article
    | Open Access

    Conventional palladium-catalyzed Heck reactions rely on the addition of oxidants and may suffer from low selectivity. Here, the authors report a nickel-catalyzed oxidative Heck arylation driven by transfer hydrogenation of an acceptor olefin leading to high E/Z selectivity and regioselectivity.

    • Honggui Lv
    • , Huiying Kang
    •  & Dongbing Zhao

  • 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

    Fluoroalkylation of C-H bonds is a class of reaction highly sought after in medicinal chemistry. Here, the authors report a regioselective organophotoredox-catalyzed, trifluoromethylthiolation of benzylic C-H bonds for a wide variety of alkyl (hetero)arenes, and demonstrate its utility in continuous flow.

    • Wentao Xu
    • , Wenliang Wang
    •  & Chengjian Zhu

  • Article
    | Open Access

    Dynamic polymer materials with reversible covalent bonds can reorganize their macromolecular architectures, and thus produce a macroscopic response to the environment. Here, the authors show dynamic covalent polyureas formed by a polyaddition reaction between pyrazoles and diisocyanates at ambient temperature in the absence of a catalyst.

    • Wen-Xing Liu
    • , Zhusheng Yang
    •  & Jian Xu

  • Article
    | Open Access

    Indole oxidation represents a fundamental organic transformation delivering valuable nitrogen compounds. Here, the authors report a general halide catalysis protocol applied to three classes of oxidation reactions of indoles with oxone as a sustainable terminal oxidant.

    • Jun Xu
    • , Lixin Liang
    •  & Rongbiao Tong

  • Article
    | Open Access

    α-Fluoromethyl arenes are common substructures in pharmaceuticals and agrochemicals but synthetic routes are still rare. Here the authors describe Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes.

    • Masakazu Nambo
    • , Jacky C.-H. Yim
    •  & Cathleen M. Crudden

  • Article
    | Open Access

    Single crystal X-ray diffraction is an invaluable tool for molecular structure determination, but growing single crystals is often an arduous process. Here the authors find that the structures of a wide array of molecules can be determined by SCXRD when included in hydrogen-bonded guanidinium organosulfonate host frameworks in a single-step crystallization.

    • Yuantao Li
    • , Sishuang Tang
    •  & Michael D. Ward

  • Article
    | Open Access

    Molecular motors have predominantly been limited to circular or linear directional motions. Here, the authors design a molecular motor that moves unidirectionally along a more complex figure-eight trajectory by a distinct four-step mechanism that alternates between photochemical and thermal reaction steps.

    • Aaron Gerwien
    • , Peter Mayer
    •  & Henry Dube

  • Article
    | Open Access

    The ring-opening and functionalization of electronically unbiased cyclopropanes is highly challenging to achieve in a regioselective fashion. Here, the authors report a mild photoredox-coupled oxoamination of electronically unactivated aryl cyclopropanes with simple azaarenes and molecular oxygen.

    • Liang Ge
    • , Ding-Xing Wang
    •  & Chao Feng

  • Article
    | Open Access

    Axially chiral compounds have widespread use in asymmetric catalysis. Here, the authors disclose a highly enantioselective synthesis of axially chiral o-naphthoquinones by chiral phosphoric acid catalysis and central-to-axial chirality conversion.

    • Shuai Zhu
    • , Ye-Hui Chen
    •  & Bin Tan

  • Article
    | Open Access

    The development of straightforward methods for the synthesis of planar chiral ferrocenes remains highly challenging. Here, the authors report a rhodium(I)/phosphonate-catalyzed thioketone-directed enantioselective C-H bond arylation reaction for the synthesis of chiral planar ferrocenes.

    • Zhong-Jian Cai
    • , Chen-Xu Liu
    •  & Shu-Li You

  • Article
    | Open Access

    Triacylglycerides are naturally abundant and renewable feedstock, but their chemical transformation is hindered by their stability. Here, under Lewis acid catalysis, the authors report the selective alkyl C–O bond conversion of triglycerides into C–N bonds and even apply this efficient method to PET depolymerization.

    • Hua Liu
    • , Yi-Ling Zhu
    •  & Zhi Li

  • Article
    | Open Access

    Due to the low ring strain and facile dimerization, ring-opening metathesis polymerization of cyclopentadiene, readily obtainable from petroleum feedstock, has not been realized. Here the authors show an ultrarapidly initiating trifluoromethanesulfonamide-based ruthenium catalyst enables it at low temperatures.

    • Kitaek Song
    • , Kunsoon Kim
    •  & Soon Hyeok Hong

  • Article
    | Open Access

    Copper-based asymmetric photocatalysis has great synthetic potential, however it has been rarely exploited due to challenges inherent to such systems. Here, a chiral bisoxazoline copper catalyst is involved in a SET process, photoredox catalysis, Lewis acid activation and asymmetric induction to construct chiral vicinal diamines.

    • Bowen Han
    • , Yanjun Li
    •  & Lei Gong

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