Organic chemistry articles within Nature Communications

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  • Article
    | Open Access

    Many natural products exist as families of structurally similar molecules, and therefore developing skeletal modifications of common intermediates offers flexible and powerful approaches for target synthesis. Here, the authors report a single-atom insertion into the framework of the benzenoid subfamily, providing access to the troponoid congeners.

    • Stefan Wiesler
    • , Goh Sennari
    •  & Richmond Sarpong

  • Article
    | Open Access

    The direct C−H-difluoromethylation of pyridines represents a highly efficient economic way to access azines. However, the direct meta-difluoromethylation of pyridines remains elusive. Here, the authors demonstrate switchable meta- as well as para-C−H difluoromethylation of pyridines through radical processes by using oxazino pyridine intermediates.

    • Pengwei Xu
    • , Zhe Wang
    •  & Armido Studer

  • Article
    | Open Access

    The direct alkenylation with simple alkenes stands out as the most ideal yet challenging strategy for obtaining high-valued desaturated alkanes. Herein, the authors present a direct asymmetric dehydrogenative α-C(sp3)-H alkenylation of carbonyls based on synergistic photoredox-cobalt-chiral primary amine catalysis under visible light.

    • Zongbin Jia
    • , Liang Cheng
    •  & Sanzhong Luo

  • Article
    | Open Access

    In recent years a growing demand for drug design approaches that incorporate a higher number of sp3-hybridized carbons fuelled the development of innovative cross-coupling strategies to reliably introduce aliphatic fragments. Here, the authors present a powerful approach for the light-mediated B-alkyl Suzuki−Miyaura crosscoupling between alkyl boranes and aryl bromides.

    • Ting Wan
    • , Luca Capaldo
    •  & Timothy Noël

  • Article
    | Open Access

    Knowledge about the full reaction signature, such as the complete profile of products and side-products is important in accelerating discovery chemistry. Here, the authors report a methodology using high-throughput experimentation and multivariate data analysis to examine Palladium- catalyzed cross-coulpling reactions.

    • George E. Clarke
    • , James D. Firth
    •  & Ian J. S. Fairlamb

  • Article
    | Open Access

    So far, only homoleptic N2 complexes of silicon have been reported under matrix-isolation conditions including but the activation of more inert nitrogen by silylenes remains challenging. Here the authors report on the activation of dinitrogen by silylenes under cryogenic conditions.

    • Liyan Cai
    • , Bing Xu
    •  & Xuefeng Wang

  • Article
    | Open Access

    Developing water compatible synthetic methods for Sulfur(VI) fluoride exchange (SuFEx) chemistry is of paramount importance. Here the authors demonstrate a catalytic dearomative [2+2] photocycloaddition that significantly speeds up the synthesis of heterocyclic alkyl SuFEx hubs, leveraging the unique reactivity at the water-oil interface.

    • Soo Bok Kim
    • , Dong Hyeon Kim
    •  & Han Yong Bae

  • Article
    | Open Access

    For the carbonylation reactions to synthesize aldehyde, ester, amide, and other carbonyl derivatives, a transition metal-free and CO- free reaction was challenging but highly demanded. Here, the authors report a transition metal-free and CO- free method for deoxygenetive/denitrogenetive conversion of phenols and anilines to aldehydes and ketones.

    • Kanak Kanti Das
    • , Debasis Aich
    •  & Santanu Panda

  • Article
    | Open Access

    Despite the established C − H deuteration of pyridine derivatives synthetic methods with good D-incorporation, under milder conditions with easy operation procedures is still on the way. Here, the authors develop a straightforward, metal-free, and acid-/base-free electrochemical C4-selective C − H deuteration of pyridine derivatives with high selectivity and excellent D-incorporation at room temperature, which use D2O as economic and convenient D-source.

    • Zhiwei Zhao
    • , Ranran Zhang
    •  & Youai Qiu

  • Article
    | Open Access

    Accessing chiral alkylamines is highly important due to their ubiquity in bioactive molecules. Here, the authors present the development of stereoretentive decarboxylative amidation of carboxylic acids using dioxazolone under ambient conditions.

    • Jeonguk Kweon
    • , Bumsu Park
    •  & Sukbok Chang

  • Article
    | Open Access

    Catalytic and enantioselective construction of chiral α,α-dialkyl indoles represents an important yet challenging objective to be developed. Herein the authors describe a cobalt catalyzed enantioselective anti-Markovnikov alkene hydroalkylation via the remote stereocontrol for the synthesis of α,α-dialkyl indoles and other N-heterocycles.

    • Jiangtao Ren
    • , Zheng Sun
    •  & Zhihui Shao

  • Article
    | Open Access

    Developing skeletal editing tools, especially to realize the single-atom transmutation in a ring system without altering the ring size is challenging. Here, the authors introduce a skeletal editing strategy that enables polycyclic arenols to be readily converted into N-heteroarenes through carbon–nitrogen transmutation.

    • Hong Lu
    • , Yu Zhang
    •  & Hao Wei

  • Article
    | Open Access

    Restricted reaction mechanism of anti-dihalogenation of alkenes makes it challenging to alter the diastereochemical course into the complementary syn-dihalogenation process. Here, the authors report a conceptually distinctive strategy for the simultaneous double electrophilic activation of the two alkene carbons from the same side to realize syn-dihalogenation.

    • Hyeon Moon
    • , Jungi Jung
    •  & Won-jin Chung

  • Article
    | Open Access

    The widespread use of organoboronic acids has prompted the development of synthetic methodologies to meet the demands on structural diversity and functional group tolerance. Herein, the authors disclose a divergent radical dechloroborylation reaction enabled by dinuclear gold catalysis with visible light irradiation.

    • Cheng-Long Ji
    • , Hongliang Chen
    •  & Jin Xie

  • Article
    | Open Access

    Developing an efficient method for the stereocontrolled synthesis of all stereoisomers of chiral hindered ethers is highly desirable but challenging. Here, the authors report an asymmetric cascade reaction catalyzed by a bimetallic catalytic system with control over the configuration of the stereocenters of tetra-aryl substituted ethers.

    • Xiangfeng Lin
    • , Xia Mu
    •  & Can Li

  • Article
    | Open Access

    Due to the electrophilic nature of arynes, it is very challenging to control chemoselectivity, when substrates possess multiple competing reaction sites. Here, the authors demonstrate that chemoselective control between two major types of benzyne transformation is accomplished by varying the 3-substituent on aryne intermediate.

    • Hongcheng Tan
    • , Shuxin Yu
    •  & Yang Li

  • Article
    | Open Access

    Compared to well-developed catalytic 1,2-diazidation of alkenes, the corresponding catalytic 1,1-diazidation of alkenes has not been realized. Here, the authors report an efficient approach for catalytic 1,1-diazidation of alkenes by redox-active selenium catalysis.

    • Wangzhen Qiu
    • , Lihao Liao
    •  & Xiaodan Zhao

  • Article
    | Open Access

    N-Glycosylated heterocycles play important roles in biological systems and drug development, but the synthesis heavily relies on ionic N-glycosylation. Herein, the authors report a dehydroxylative radical method for synthesizing N-glycosides by leveraging copper metallaphotoredox catalysis.

    • Da-Peng Liu
    • , Xiao-Sen Zhang
    •  & Xiang-Guo Hu

  • Article
    | Open Access

    Polarizability, a property that is closely related to softness in the classic theory of Hard and Soft Acids and Bases (HSAB), has been largely overlooked in connecting with enantio-selection in the past. Here, the authors show local polarizability-based electronic effects can rationalize a wide range of stereochemical outcomes in widely-known asymmetric catalytic reactions.

    • Fumin Chen
    • , Yu Chen
    •  & Xiangyou Xing

  • Article
    | Open Access

    The synthesis of sequence-regulated oligosulfates has not yet been established due to the difficulties in precise reactivity control. Here, the authors report a multi-directional divergent iterative method to furnish oligosulfates based on a chain homologation approach, in which the fluorosulfate unit is regenerated.

    • Min Pyeong Kim
    • , Swatilekha Kayal
    •  & Sung You Hong

  • Article
    | Open Access

    Developing facile and direct synthesis routes for enantioselective construction of cyclic π-conjugated molecules is crucial but the chirality orginiating from the distorted structure around heptagon-containing polyarenes is largely overlooked. Herein the authors present a highly enantioselective synthesis for fabrication of all carbon heptagon-containing polyarenes via palladium-catalyzed carbene-based cross–coupling of benzyl bromides and N-arylsulfonylhydrazones.

    • Huan Zhang
    • , Chuan-Jun Lu
    •  & Ren-Rong Liu

  • Article
    | Open Access

    Exploitation of noncovalent interactions has received much attention for the design of metal catalysts. However, because of the weak nature, CH-π interactions have been less utilized for the control of organic reactions. Here, the authors report that the CH-π interaction can be used to kinetically accelerate catalytic C-H activation of arenes.

    • Yushu Jin
    • , Boobalan Ramadoss
    •  & Laurean Ilies

  • Article
    | Open Access

    Multiple autocatalytic reactions producing thiols are known, but negative feedback loop motifs are unavailable for thiol chemistry. Here, the authors develop a negative feedback loop based on the selenocarbonates, in which thiols induce the release of aromatic selenols that catalyze the oxidation of thiols by organic peroxides.

    • Xiuxiu Li
    • , Polina Fomitskaya
    •  & Sergey N. Semenov

  • Article
    | Open Access

    The stereospecific Z/E isomerization of tetrasubstituted alkenes remains underdeveloped, thus lacking in a stereodivergent synthesis of axially chiral alkenes. Here, authors report the atroposelective synthesis of tetrasubstituted alkene analogues by asymmetric allylic substitution-isomerization, followed by the photocatalyzed Z/E isomerization.

    • Jie Wang
    • , Jun Gu
    •  & Ying He

  • Article
    | Open Access

    Planar chiral [2.2]paracyclophanes have a wide range of applications in asymmetric synthesis and materials science. However, they are accessed via time-consuming chiral separations or kinetic resolution approaches. Here, the authors report a simple, metal-free protocol for organocatalytic desymmetrization of prochiral diformyl[2.2]paracyclophanes.

    • Vojtěch Dočekal
    • , Filip Koucký
    •  & Jan Veselý

  • Article
    | Open Access

    Divergent functionalizations of pi bonds allow for synthetic chemists to move from simplicity to complexity. Here, the authors report a nickel-catalyzed switchable arylation/cyclization of 1,6-enynes in which the nature of the ligand dictates the regioselectivity of alkyne arylation, while the electrophilic trapping reagents determine the selectivity of the cyclization mode.

    • Wenfeng Liu
    • , Wei Li
    •  & Wangqing Kong

  • Article
    | Open Access

    Cross-dehydrogenative coupling (CDC) of C-H bonds is an ideal approach for C-C bond construction but suffers from low selectivity of similar C-H bonds. Here, the authors describe a highly selective paired electrocatalysis strategy towards CDC combining hydrogen evolution reaction catalysis with hydride transfer catalysis.

    • Ke Liu
    • , Mengna Lei
    •  & Sheng Zhang

  • Article
    | Open Access

    Controlling regioselectivity is one of the most challenging aspects for the construction of aryl boron compounds, and there are few practical and general strategies for such transformations. Here, the authors report an iridium-catalyzed trialkoxysilane protecting group-assisted regioselective C–H borylation with various aromatic compounds.

    • Guodong Ju
    • , Zhibin Huang
    •  & Yingsheng Zhao

  • Article
    | Open Access

    C-oligosaccharides are found in natural products and drug molecules, but their synthesis is challenging. Here, the authors report a strategy for the stereoselective and efficient synthesis of Coligosaccharides via palladium-catalyzed nondirected C1–H glycosylation/C2-alkenylation, cyanation, and alkynylation of 2-iodoglycals with glycosyl chloride donors.

    • Ya-Nan Ding
    • , Mei-Ze Xu
    •  & Yong-Min Liang

  • Article
    | Open Access

    The reduction of unactivated alkyl alkenes is a difficult challenge in organic chemistry. Here, the authors present a silicon-mediated electroreduction of alkyl alkenes, using water as a hydrogen source, enabled by [Fe]-H.

    • Yanwei Wang
    • , Qian Wang
    •  & Youai Qiu

  • Article
    | Open Access

    The direct reductive coupling of alkyl alcohol and aryl halide enables efficient access to valuable compounds, but the asymmetric pattern remains unknown. Here the authors describe the enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohol and aryl bromide in the presence of an NHC activating agent.

    • Li-Li Zhang
    • , Yu-Zhong Gao
    •  & Ze-Peng Yang

  • Article
    | Open Access

    The Ganoderma meroterpenoids are a growing class of natural products with a wide range of biological activities. Here, the authors report the enantioselective total synthesis of the Ganoderma meroterpenoid (‒)-lucidumone, featuring a copper-catalyzed enantioselective silicon-tethered intramolecular Diels-Alder cycloaddition to assemble the bicyclo[2.2.2]octane framework and a domino deprotection/Prins reaction/cycloetherification/oxidation sequence to generate concurrenly the tetrahydrofuran and the fused indanone skeleton.

    • Xian-Zhang Liao
    • , Ran Wang
    •  & Guang Li

  • Article
    | Open Access

    While the homo N-N coupling of two NH moieties to form the hydrazide N-N bond is well developed, the crossdehydrogenative hetero N-N coupling remains unevolved. Here the authors present an efficient, PhI(OAc)2-mediated intermolecular N-N cross-coupling of primary benzamides with primary and secondary amines.

    • Subban Kathiravan
    • , Prakriti Dhillon
    •  & Ian A. Nicholls

  • Article
    | Open Access

    Carbon isotope labelling of bioactive molecules is essential for accessing the pharmacokinetic and pharmacodynamic properties of new drug entities. Here, the authors propose an electrochemical isotope-labelling protocol which enables the use of near-stoichiometric 14CO2, facilitating late-stage and single-step carbon-14 labelling of pharmaceuticals and representative precursors.

    • Gabriel M. F. Batista
    • , Ruth Ebenbauer
    •  & Troels Skrydstrup

  • Article
    | Open Access

    Prostaglandins are of interest to synthetic chemists due to their biological activities. Here, the authors present a concise chemoenzymatic synthesis method for several representative prostaglandins, achieved in 5 to 7 steps, via the common intermediate bromohydrin, a radical equivalent of Corey lactone.

    • Yunpeng Yin
    • , Jinxin Wang
    •  & Jian Li

  • Article
    | Open Access

    P-stereogenic heterocycles are privileged chiral ligands and bioactive compounds, but the catalytic asymmetric synthesis of P-stereogenic phosphindane derivatives is challenging. Here, the authors report a catalytic kinetic resolution of phosphindole oxides via rhodium-catalyzed diastereo- and enantioselective conjugate addition to access enantiopure Pstereogenic phosphindane and phosphindole derivatives.

    • Long Yin
    • , Jiajia Li
    •  & Dong Guo

  • Article
    | Open Access

    Chemically modified nucleobases and oligonucleotides are essential in several fields but introducing functional groups into nucleobases requires laborious chemical synthesis. Here, the authors report site-selective alkylation at the C8-position of guanines in guanosine, GMP, GDP, and GTP, as well as late-stage alkylation of RNA/DNA oligonucleotides through photomediated Minisci reaction.

    • Ruoqian Xie
    • , Wanlu Li
    •  & Gang Chen

  • Article
    | Open Access

    Polyketide macrolides are of interest for drug discovery but their inherent structural and stereochemical complexity hinders the exploration of related regions of chemical space more broadly. Here, the authors designed in silico and synthesized a library of tetrahydrofuran-containing polyketide macrolides, and screened them against a panel of biological assays, identifying biologically active library members.

    • Darryl M. Wilson
    • , Daniel J. Driedger
    •  & Robert A. Britton

  • Article
    | Open Access

    Medium-sized-ring compounds are challenging synthetic targets in organic chemistry. Here the authors report an intramolecular dearomative [5 + 4] cycloaddition of naphthalene-derived vinylcyclopropanes to construct these molecules under visible-light irradiation and a proper triplet photosensitizer.

    • Min Zhu
    • , Yuan-Jun Gao
    •  & Shu-Li You

  • Article
    | Open Access

    Reactive sulfane sulfur species such as persulfides and H2S2 are important redox regulators and linked to H2S signaling, but their study is hindered by a lack of suitable donors to produce them. Here, the authors report 2H-thiopyran-2-thione sulfine (TTS), a compound which can specifically convert H2S to HSOH, and then to H2S2 in the presence of excess H2S.

    • Qi Cui
    • , Meg Shieh
    •  & Ming Xian

  • Article
    | Open Access

    Phenols and anilines are of extreme importance for medicinal chemistry and material science but the selective preparation of meta-substituted phenols and anilines remains challenging. Here the authors report an efficient copper-catalyzed dehydrogenation strategy to exclusively synthesize meta-carbonyl phenols and anilines from carbonyl substituted cyclohexanes.

    • Bao-Yin Zhao
    • , Qiong Jia
    •  & Yong-Qiang Wang

  • Article
    | Open Access

    Combining data science and organic synthesis to achieve the rapid and precise creation of complex molecules while controlling multiple selectivities is an emerging trend, but few successful examples are reported. Here, the authors develop an artificial neural network regression model using bond orbital data to predict chemical reactivities.

    • Shingo Harada
    • , Hiroki Takenaka
    •  & Tetsuhiro Nemoto

  • Article
    | Open Access

    Characterizing highly-reactive glycosyl cation intermediates and understanding their glycosylation mechanisms are essential to the stereoselective synthesis of complex carbohydrates. Here the authors report a workflow that is utilized to characterize rhamnosyl 1,3-bridged dioxanium ions derived from C-3 p-anisoyl esterified donors.

    • Peter H. Moons
    • , Floor ter Braak
    •  & Thomas J. Boltje

  • Article
    | Open Access

    Site- and stereoselective C–H functionalization is challenging in the synthetic chemistry, and the catalytic enantioselective C(sp3)–H functionalization based on vinyl cations has scarcely explored. Here, the authors report an asymmetric copper-catalyzed tandem diyne cyclization/unactivated C(sp3)–H insertion reaction via a kinetic resolution.

    • Yang-Bo Chen
    • , Li-Gao Liu
    •  & Long-Wu Ye

  • Article
    | Open Access

    Stereodefined vinylboron compounds are important organic synthons, but the selective generation of the thermodynamically unfavorable Z-isomers remains challenging. Here, the authors develop a cobalt catalytic system, enabling the transformation of terminal alkynes with excellent Z-selectivity, even in the presence of bulky substituents.

    • Jinglan Wen
    • , Yahao Huang
    •  & Peng Hu

  • Article
    | Open Access

    The development of stable and efficient ligands is of vital significance to enhance the catalytic performance of carbonylation reactions of alkenes. Here, the authors develop an aryldiphosphine ligand, used in palladium-catalyzed regioselective carbonylation of alkenes, exhibiting high catalytic performance and strong oxygen-resistance stability.

    • Kang Zhao
    • , Hongli Wang
    •  & Feng Shi

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