Organic chemistry articles within Nature Communications

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  • Article
    | Open Access

    Chiral and hindered triazolopyridinone derivatives are an underexplored area of chemical space mainly due to their challenging synthesis via classical methods. Here, the authors report an electrochemical rearrangement for the synthesis of triazolopyridinones using diverse, available alkyl carboxylic acids as starting materials.

    • Zenghui Ye
    • , Yanqi Wu
    •  & Fengzhi Zhang

  • Article
    | Open Access

    Extracting experimental operations for chemical synthesis from procedures reported in prose is a tedious task. Here the authors develop a deep-learning model based on the transformer architecture to translate experimental procedures from the field of organic chemistry into synthesis actions.

    • Alain C. Vaucher
    • , Federico Zipoli
    •  & Teodoro Laino

  • Article
    | Open Access

    Structurally divergent reactions on racemic mixtures, which produce distinct chemical species from an enantiomeric mixture, are extremely rare in the literature. Here, the authors are able to use a dynamic combinatorial approach to yield structurally divergent, non-isomeric [2]catenanes from an enantiomeric mixture.

    • Tiberiu-M. Gianga
    •  & G. Dan Pantoș

  • Article
    | Open Access

    Heteroatom-bearing molecular loops and belts are fascinating but generally difficult to synthesize. Here, the authors demonstrate that O,S-bridged double-stranded molecular belts—cyclophenoxathiins—can be successfully constructed and employed as versatile supramolecular hosts.

    • Jialin Xie
    • , Xia Li
    •  & Kelong Zhu

  • Article
    | Open Access

    Due to their abundance and importance in organic chemistry, development of methods for ketone synthesis is essential. Here, the authors report a photoredox, nickel and phosphoranyl radical synergistic cross-electrophile coupling of aromatic acids and aryl/alkyl bromides to directly synthesise ketones.

    • Rehanguli Ruzi
    • , Kai Liu
    •  & Jin Xie

  • Article
    | Open Access

    Realizing efficient n-doping in organic thermoelectrics remains a challenge due to dopant-semiconductor immiscibility, poor dopant stability and low doping efficiency. Here, the authors use computer-assisted screening to develop n-dopants for thermoelectric polymers that show record power factors.

    • Chi-Yuan Yang
    • , Yi-Fan Ding
    •  & Jian Pei

  • Article
    | Open Access

    Catalytic reductive coupling of two electrophiles and one C = C bond is usually performed by two electron transfer metal catalysis. Herein, the authors show a visible light photoredox-catalyzed successive single electron transfer leading to dearomative arylcarboxylation of indoles with CO2 and generating indoline-3-carboxylic acids.

    • Wen-Jun Zhou
    • , Zhe-Hao Wang
    •  & Da-Gang Yu

  • Article
    | Open Access

    Flavins and deazaflavins are well suited for photoredox processes but their application in photoreductions is challenging. Here, the authors provide direct evidence of the high reductive power of excited deazaflavin semiquinones and their application in catalytic photodehalogenations.

    • Andreas Graml
    • , Tomáš Neveselý
    •  & Burkhard König

  • Article
    | Open Access

    Amides are versatile synthetic building blocks, however the general stability of the amide bond makes its selective transformation challenging. Here, the authors report a chemodivergent transformation of primary, secondary and tertiary amides by using 1,1-diborylalkanes as pro-nucleophiles.

    • Wei Sun
    • , Lu Wang
    •  & Chao Liu

  • Article
    | Open Access

    Carbon atoms of various species typically function as acceptors of noncovalent interactions when they are part of a π-system. Here, the authors report their discovery of a noncovalent halogen bond involving the isocyano carbon lone pair, which results in adducts with strongly reduced isocyanide odor.

    • Alexander S. Mikherdov
    • , Alexander S. Novikov
    •  & Vadim Yu. Kukushkin

  • Article
    | Open Access

    Cross-coupling processes without the use of transition metals are challenging to achieve. Here, the authors show a transition-metal-free cross-coupling utilizing aryl(heteroaryl) methyl sulfoxides and alcohols to afford alkyl aryl(heteroaryl) ethers and propose a nucleophilic addition mechanism based on experiments and theory.

    • Guolin Li
    • , Yexenia Nieves-Quinones
    •  & Tiezheng Jia

  • Article
    | Open Access

    Benzylic oxygenation of methylarenes is a direct but challenging method for aldehyde synthesis from simple starting materials. Here, the authors show an electrochemical, site-selective method for the oxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition metal catalysts.

    • Peng Xiong
    • , Huai-Bo Zhao
    •  & Hai-Chao Xu

  • Article
    | Open Access

    Dioxolenium ion intermediates formed from remote positions are hypothesized to direct stereoselective glycosylations. Herein we combine infrared ion spectroscopy, DFT calculations and synthetic work to characterize and study these dioxolenium ions and their role in stereoselective glycosylation reactions.

    • Thomas Hansen
    • , Hidde Elferink
    •  & Thomas J. Boltje

  • Article
    | Open Access

    Selective C-H trifluoromethoxylation of pyridines remains a formidable synthetic challenge. Here, the authors report a silver-mediated late-stage C-H trifluoromethoxylation of arenes and heteroarenes as limiting reagents with trifluoromethoxide anion.

    • Zhijie Deng
    • , Mingxin Zhao
    •  & Pingping Tang

  • Article
    | Open Access

    Control of cysteine reactivity is of paramount importance for the synthesis of proteins using native chemical ligation. Here, the authors report a readily cleavable N-selenoethyl group attached to cysteine and apply it to the modular assembly of linear and cyclic polypeptides.

    • Vincent Diemer
    • , Nathalie Ollivier
    •  & Oleg Melnyk

  • Article
    | Open Access

    Tandem Heck/carbonylation reaction gives access to ubiquitous carbonyl molecules, however the asymmetric version is rarely studied. Here, the authors synthesize chiral bicyclo[3.2.1]octanes with a palladium-catalyzed asymmetric tandem Heck/carbonylation desymmetrization of cyclopentenes with alcohols, phenols and amines.

    • Zhenbo Yuan
    • , Yuye Zeng
    •  & Hequan Yao

  • Article
    | Open Access

    Arene dearomatization reactions allow chemists to rapidly build unique chemical architectures from largely available starting materials. Here, the authors show a photocatalytic carboamination/dearomatization cascade process leading to 1,4-cyclohexadiene-fused sultams via N-centered radicals.

    • Rory C. McAtee
    • , Efrey A. Noten
    •  & Corey R. J. Stephenson

  • Article
    | Open Access

    [2 + 2] cycloaddition of alkynes with alkenes would normally require UV light irradiation. Here, the authors report an alkyne–alkene [2 + 2] cycloaddition based on visible light energy transfer photocatalysis, both inter- and intramolecularly, to afford cyclobutenes and 1,3-dienes.

    • Sujin Ha
    • , Yeji Lee
    •  & Cheol-Min Park

  • Article
    | Open Access

    Diatomic carbon (C2) is historically an elusive chemical species, considered to require high physical energy for its generation. Here, the authors describe the first room-temperature chemical synthesis of C2 and present experimental evidence for its singlet biradical (quadruple bonding) character and role as a molecular element of nanocarbons.

    • Kazunori Miyamoto
    • , Shodai Narita
    •  & Masanobu Uchiyama

  • Article
    | Open Access

    Dehydrogenative alkenylation of C-H bonds is an atom-economical approach to prepare more complex olefins. Here, the authors use a combination of decatungstate and a cobaloxime catalyst for the photocatalytic dehydrogenative alkenylation of alkanes and aliphatic aldehydes with aryl alkenes.

    • Hui Cao
    • , Yulong Kuang
    •  & Jie Wu

  • Article
    | Open Access

    Bryostatin 1 is a unique therapeutic lead, however its scarce natural sources have hampered its use in treatment of human disease. Here, the authors use a scalable synthesis of bryostatin 1 to make close-in analogs which potently induce increased cell surface expression holding potential for immunotherapy.

    • Clayton Hardman
    • , Stephen Ho
    •  & Paul A. Wender

  • Article
    | Open Access

    Replacing carbon atoms in nanocarbons with heteroatoms alters their intrinsic properties, and nitrogen-doped nanocarbons attract much attention in various fields. Here, the authors synthesize a discrete nitrogen-doped nanotube molecule and clarify its structure to reveal unique features of nitrogen dopants.

    • Koki Ikemoto
    • , Seungmin Yang
    •  & Hiroyuki Isobe

  • Article
    | Open Access

    Gridarenes with well-defined edges and vertices represent versatile nanoscale building blocks for installating frameworks but suffer from lack of stereoselective control during their synthesis. Here, the authors report a diastereoselective gridization of superelectrophilic diazafluorene-containing substrates with crescent shapes into Drawing Hands grids (DHGs).

    • Dongqing Lin
    • , Ying Wei
    •  & Wei Huang

  • Article
    | Open Access

    Strategies for enantioselective α-aminomethylation of carbonyl compounds rely on the chiral activation of stable ketones substrate. Here, the authors report a rhodium/chiral phosphoric acid cooperative catalysis for the three-component reaction of α-diazo ketones with alcohols and 1,3,5-triazines via imine chiral activation.

    • Jiuwei Che
    • , Li Niu
    •  & Wenhao Hu

  • Article
    | Open Access

    C-N bond forming is an established strategy to form amines, which are quintessential in chemical synthesis and in nature. Here, the authors report three classes of photoredox reactions, involving C(sp3)-N coupling between N-centered radicals and alkyl radicals and C(sp3)- C(sp3) coupling via C(sp3)-H alkylation.

    • Quanping Guo
    • , Qiang Peng
    •  & Zhaoqing Xu

  • Article
    | Open Access

    Long-lived carbon nitride radicals have been used in several photocatalytic reactions. Herein, long-lived potassium poly(heptazine imide) radicals enable synthesis of γ,γ-dichloroketones from enones by addition of CHCl2 moiety, generated from chloroform, to the C=C bond.

    • Stefano Mazzanti
    • , Bogdan Kurpil
    •  & Aleksandr Savateev

  • Article
    | Open Access

    Traditional synthesis of stereodefined piperidines requires selective installation of functional groups that can lower efficiency and modularity. Here, the authors assemble stereochemically complex and highly substituted dehydropiperidines via an intermolecular ring expansion between bicyclic aziridines and Rh-supported vinyl carbenes.

    • Josephine Eshon
    • , Kate A. Nicastri
    •  & Jennifer M. Schomaker

  • 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

    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

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