Organic chemistry articles within Nature Communications

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  • Article
    | Open Access

    Bicyclo[1.1.1]pentanes (BCPs) are important motifs in contemporary drug design, however, approaches to BCPs featuring adjacent stereocenters are rather limited. Here, the authors report a photo- and organocatalyzed asymmetric addition of simple aldehydes to [1.1.1]propellane to generate enantioenriched α-chiral BCPs.

    • Marie L. J. Wong
    • , Alistair J. Sterling
    •  & Edward A. Anderson

  • Article
    | Open Access

    Incommensurate pairing is a type of stereoisomerism, observed in carbon bilayers, that arises from the twisted orientations of the graphitic layers. Here, the authors create a finite molecular version of an incommensurate carbon bilayer in the form of two concentrically assembled cylindrical molecules.

    • Taisuke Matsuno
    • , Yutaro Ohtomo
    •  & Hiroyuki Isobe

  • Article
    | Open Access

    Iron is an essential plant nutrient that is poorly bioavailable in alkaline soils, resulting in reduced agricultural productivity. Here, the authors report the synthesis of stable and cheap iron-chelator, proline-2’-deoxymugineic acid (PDMA), and demonstrate its utility as potential fertilizer.

    • Motofumi Suzuki
    • , Atsumi Urabe
    •  & Kosuke Namba

  • Article
    | Open Access

    Geometric E to Z double C=C bond isomerization is challenging as it requires kinetic trapping of the Z-isomer with injection of chemical energy. Here, the authors report a dinuclear Pd(I)−Pd(I) complex that mediates selective isomerization of E-1,3-dienes to the Z-isomers without photoirradiation.

    • Eiji Kudo
    • , Kota Sasaki
    •  & Tetsuro Murahashi

  • Article
    | Open Access

    Site-selective C–H functionalization still faces some challenges, such as the introduction and removal of an appropriate directing group. Here, the authors introduce a temporary directing group for selective meta-C–H functionalization of 2-arylbenzaldehydes via reversible imine formation.

    • Sukdev Bag
    • , Sadhan Jana
    •  & Debabrata Maiti

  • Article
    | Open Access

    Furanocembranoid-like natural products with the alkene-substituted furan scaffold display a range of biological activities, but are difficult to access. Here, the authors report a modular biomimetic strategy to synthesise diverse alkene-substituted furan-containing macrolactams via palladium-catalysed unactivated Csp3-H olefination.

    • Jiping Hao
    • , Xueying Guo
    •  & Weibo Yang

  • Article
    | Open Access

    Metal carbene is usually employed as a 1-carbon synthon or 3-carbon synthon in a variety of cycloaddition reactions. Here, the authors report a gold-catalyzed cascade protocol for the assembly of polycarbocyclic frameworks via a β-aryl gold-carbene intermediate which reacts as a 4-carbon synthon with alkenes in [4 + 2]-cycloadditions.

    • Cheng Zhang
    • , Kemiao Hong
    •  & Xinfang Xu

  • Article
    | Open Access

    Due to the ionic nature of its mechanism, the Mannich reaction can only use non-enolizable aldehydes as substrates. Here, the authors expand the scope of the classical Mannich reaction to enolizable aldehydes by employing a radical process resulting in a streamlined synthesis of γ-amino-carbonyl compounds.

    • Shuai Shi
    • , Wenting Qiu
    •  & Zhankui Sun

  • Article
    | Open Access

    The use of alkyl chlorides in Pd-catalyzed Mizoroki–Heck coupling reactions remains an unsolved problem despite their significant synthetic potential. Here, the authors show that alkyl chlorides can efficiently participate in Mizoroki–Heck cross-coupling reactions with excellent functional group compatibility via photoinduced Pd catalysis.

    • Geun Seok Lee
    • , Daeun Kim
    •  & Soon Hyeok Hong

  • Article
    | Open Access

    The synthesis of regio- and stereo-defined alkenes with multiple alkyl substituents is an unmet challenge. Here, the authors report a nickel-catalyzed intermolecular cross-dialkylation of alkynes devoid of directing or activating groups to afford multiple aliphatic substituted alkenes in a syn-selective fashion.

    • Yi-Zhou Zhan
    • , Nan Xiao
    •  & Wei Shu

  • Article
    | Open Access

    Synthesis of peptides and proteins containing multiple disulfide bonds is challenging, limiting the elucidation of their biological functions. Here, the authors report a general synthetic strategy for fast formation of two and three disulfide bonds in peptides and proteins, and apply it to prepare several therapeutically important peptides.

    • Shay Laps
    • , Fatima Atamleh
    •  & Ashraf Brik

  • Article
    | Open Access

    β-Hydrogen elimination is a fundamental reaction in palladium catalysis, however, the eliminated β-hydrogen is usually attached to a sp3-carbon. Here, the authors report a palladium-catalyzed cross-coupling reaction involving a β-vinylic hydrogen elimination from an allylic palladium intermediate.

    • Ge Zhang
    • , Yi-Kang Song
    •  & Guo-Qiang Lin

  • Article
    | Open Access

    Chiral benzylamines are found in many pharmacologically active molecules. Here, the authors report an enantio- and regio-selective reductive hydroarylation of N-acyl enamines with a NiH/chiral bis-imidazoline catalytic system affording a range of enantioenriched benzylamines.

    • Yuli He
    • , Huayue Song
    •  & Shaolin Zhu

  • Article
    | Open Access

    Covalently 2D-patterning graphene with different chemical functionalities is an attractive way to tailor its physical and chemical properties. Here, the authors realize spatially defined 2D-hetereoarchitectures of graphene via a strategy of molecular embroidering.

    • Tao Wei
    • , Malte Kohring
    •  & Andreas Hirsch

  • Perspective
    | Open Access

    Enantioselective functionalization of ubiquitous C(sp3)–H bonds via radical species has witnessed a renaissance in the past years. Here, the authors summarize the main achievements in the field by identifying two main reaction pathways determining the stereochemistry and give an outlook on future challenges and opportunities.

    • Chi Zhang
    • , Zhong-Liang Li
    •  & Xin-Yuan Liu

  • Article
    | Open Access

    Multicomponent reactions enable the rapid construction of diverse molecular scaffolds with modularity and step economy. In this work, the authors report the use of boronic acids as carbon nucleophiles in a Passerini-type three-component coupling reaction towards an expanded inventory of α-hydroxyketones.

    • Kai Yang
    • , Feng Zhang
    •  & Qiuling Song

  • Article
    | Open Access

    Organocatalytic atom transfer radical polymerization (O-ATRP) is attractive due to its metal-free nature but catalysts are rarely applied at a low loading. Here the authors introduce a catalyst design logic based on heteroatom-doping of polycyclic arenes, which led to the discovery of oxygen-doped anthanthrene as an organic photoredox catalysts for O-ATRP.

    • Qiang Ma
    • , Jinshuai Song
    •  & Saihu Liao

  • Article
    | Open Access

    Chiral acetylenic derivatives are found in many bioactive compounds and are versatile building blocks in organic synthesis. Here, the authors report a mild enantioselective nickel/Lewis acid-catalyzed asymmetric propargylic substitution reaction which is applied to the collective synthesis of seven biologically active compounds.

    • Xihao Chang
    • , Jiayin Zhang
    •  & Chang Guo

  • Article
    | Open Access

    Thiol-disulfide exchange is an extensively used reversible reaction in dynamic combinatorial chemistry, but usually requires long time to reach equilibrium. Here, the authors employ selenocystine as a catalyst of thiol-disulfide exchange at low temperatures and basic pH, and show that it can promote disulfide bond formation during folding of a scrambled RNase A.

    • Andrea Canal-Martín
    •  & Ruth Pérez-Fernández

  • Article
    | Open Access

    Dynamic kinetic resolution is a common approach for the preparation of optically pure amino acids using enzymes. Here the authors report an alternative method based on enantioselective extraction coupled with racemization, in which a bulky extractant affords hydrophobic extractable imines with amino acids rapidly, reversibly and enantioselectively.

    • Haofei Huang
    • , Yingji Jin
    •  & Kwan Mook Kim

  • Article
    | Open Access

    Several Hasubanan alkaloids have been synthesized in the past decades, however a divergent approach to access the 3 subclasses of such natural products has not been reported yet. Here, the authors show the enantioselective total syntheses of four representative members via a unified strategy leading to the three topologically different classes of alkaloids.

    • Guang Li
    • , Qian Wang
    •  & Jieping Zhu

  • Article
    | Open Access

    Bis-silylated alkenes offer the advantage of two functional handles with distinguished reactivity for downstream functionalization. Here, the authors report a nickel-catalyzed bis-silylation of internal alkynes to versatile silylated alkene intermediates which can be chemoselectively manipulated.

    • Yun Zhang
    • , Xi-Chao Wang
    •  & Dongbing Zhao

  • Article
    | Open Access

    Vitamin B3 derivatives display a range of biological activities. Here, the authors report the synthesis of meta-aminoaryl nicotinates, derivatives of vitamin B3, and their late-stage conjugation with (hetero)arylamines, ultimately expanding the chemical space for biomedical research.

    • Begur Vasanthkumar Varun
    • , Kannan Vaithegi
    •  & Seung Bum Park

  • Article
    | Open Access

    C-nucleosides are analogues of the canonical N-nucleosides and, despite their synthetic value, biocatalysis has not targeted them yet. Here, the authors report a pseudouridine monophosphate C-glycosidase enzyme for selective 5-β-C-glycosylation of uracil and its derivatives from pentose 5- phosphate substrates.

    • Martin Pfeiffer
    •  & Bernd Nidetzky

  • Article
    | Open Access

    Xenon binding carries potential for xenon separation and emerging applications in magnetic resonance imaging. Here, the authors report a rare example of a tight yet soft capsule, assembled from two chiral bisurea-bisthiourea macrocycle components, that can efficiently and adaptively bind xenon in both the solid state and solution.

    • Shi-Xin Nie
    • , Hao Guo
    •  & Qi-Qiang Wang

  • Article
    | Open Access

    The reactivity of expanded porphyrins is highly influenced by their scaffold architecture. Here, the authors construct two nonaromatic dumbbell-shaped benzene- and pyridine-incorporating octaphyrins via Suzuki-Miyaura cross-coupling; depending on the framework, different coordination modes are obtained upon metallation with Pd(II).

    • Le Liu
    • , Zhiwen Hu
    •  & Jianxin Song

  • Article
    | Open Access

    Alcohols are more naturally abundant than carbonyl compounds, which in turn are well known for their reactivity in Grignard reactions. Here, the authors showcase a distinct Grignard-like reactivity by using alcohols as coupling partners with hydrazones and synthesize more complex alcohols under ruthenium catalysis.

    • Chen-Chen Li
    • , Haining Wang
    •  & Chao-Jun Li

  • Article
    | Open Access

    Metal-free olefin diamination may display challenges, especially when targeting fluorinated amines. Here, the authors report a double nucleophilic functionalization of an activated alkene originated from a trifluoropropenyliodonium salt with two nucleophiles for the selective synthesis of trifluoromethylated ethylene amines and diamines.

    • Ferenc Béke
    • , Ádám Mészáros
    •  & Zoltán Novák

  • Article
    | Open Access

    Selective manipulation of one functional group, out of many repeatedly occurring in a substrate, represents a grand challenge in chemistry. Here, the authors report a Pd/Lewis acid cocatalytic system that achieves not only site-selective, but also site-switchable mono-O-allylation of polyols.

    • Hua Tang
    • , Yu-Biao Tian
    •  & Dawen Niu

  • Article
    | Open Access

    Chiral functional materials with circularly polarized luminescence can be used in various applications but rarely reported. Here the authors show, a complex system, which show intense circularly polarized ultraviolet luminescence with large glum value, enabling a chiral UV light triggered enantioselective polymerization.

    • Dongxue Han
    • , Xuefeng Yang
    •  & Pengfei Duan

  • Article
    | Open Access

    Combining the Heck reaction with other transformations provides a powerful strategy to access diverse, complex compounds. Here, the authors report a weak coordination dominated Pd(0)-catalyzed quadruple C-H activation followed by hydro-functionalization, C-H silylation, and C-H borylation.

    • Bo-Cheng Tang
    • , Wen-Xuan Lin
    •  & An-Xin Wu

  • Article
    | Open Access

    Skeletal reorganizations are intriguing processes in chemical synthesis due to their mechanism, atom-economy and synthetic versatility. Herein, the authors describe a divergent skeletal reorganization of N-sulfonyl ynamides to thiete sulfones and propargyl sulfonamides.

    • Linwei Zeng
    • , Yuxin Lin
    •  & Sunliang Cui

  • Article
    | Open Access

    Development of algorithms to predict reactant and reagents given a target molecule is key to accelerate retrosynthesis approaches. Here the authors demonstrate that applying augmentation techniques to the SMILE representation of target data significantly improves the quality of the reaction predictions.

    • Igor V. Tetko
    • , Pavel Karpov
    •  & Guillaume Godin

  • Article
    | Open Access

    Despite of the high demand of chiral allenes, their asymmetric synthesis remains a challenge for organic chemists. Here, the authors report a stereodivergent synthesis of trisubstituted allenes via asymmetric additions of oxazolones to activated 1,3-enynes enabled by modification of chiral phosphoric acid catalysts.

    • Jiawen Wang
    • , Sujuan Zheng
    •  & Xiaoyu Yang

  • Article
    | Open Access

    Catalytic asymmetric conjugate allylation of unsaturated carbonyl compounds is usually difficult to achieve due to competing 1,2-addition. Here, the authors report a copper(I)-catalyzed asymmetric 1,6-conjugate allylation of 2,2-dimethyl-6-alkenyl-4H-1,3-dioxin-4-ones with good scope and high enantioselectivity.

    • Chang-Yun Shi
    • , Zhi-Zhou Pan
    •  & Liang Yin

  • Article
    | Open Access

    Synthetic methods aiming at minimizing reaction steps while increasing molecular complexity are highly sought after by organic chemists. Here, the authors report two cascade procedures combining nucleophilic substitution, palladium-catalyzed Heck and C–H activation reactions for the synthesis of spiro-fused heterocycles.

    • Fei Ye
    • , Yao Ge
    •  & Matthias Beller

  • Article
    | Open Access

    Thiols are important precursors for the synthesis of a variety of pharmaceutically important sulfur-containing compounds. Here, the authors report a visible light-mediated decarboxylative thiolation of alkyl redox-active esters to free thiols and the in situ product diversification of a number of thiol derivatives.

    • Tianpeng Cao
    • , Tianxiao Xu
    •  & Saihu Liao

  • Article
    | Open Access

    Direct catalytic C(sp2)–H alkylation of unactivated arenes with alkyl halides remains elusive despite the progress in C-H functionalization. Here, the authors report the catalytic C(sp2)–H alkylation of unactivated arenes with alkyl bromides via visible-light induced Pd catalysis.

    • Daeun Kim
    • , Geun Seok Lee
    •  & Soon Hyeok Hong

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