Organic chemistry articles within Nature

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  • News & Views |

    The idea that three different free radicals could be used together to carry out specific steps in a chemical reaction has long been implausible. A ‘radical sorting’ strategy now achieves this feat to make organic molecules.

    • Kenneth F. Clark
    •  & John A. Murphy

  • Article |

    A couple-close approach used to build semisaturated ring systems from dual radical precursors allows sampling of regions of underexplored chemical space, leading to an annulation that can be used for late-stage functionalization of pharmaceutical scaffolds.

    • Alice Long
    • , Christian J. Oswood
    •  & David W. C. MacMillan

  • Article |

    We use bimolecular homolytic substitution catalysis to sort an electrophilic radical and a nucleophilic radical across an unactivated alkene, accelerating access to pharmaceutically relevant C(sp3)-rich molecules and defining a mechanistic approach for alkene dialkylation.

    • Johnny Z. Wang
    • , William L. Lyon
    •  & David W. C. MacMillan

  • Article
    | Open Access

    We introduce a method for the direct 1,3-difunctionalization of alkenes, based on a concept termed ‘charge relocation’, which enables stereodivergent access to 1,3-difunctionalized products of either syn- or anti-configuration from unactivated alkenes.

    • Bogdan R. Brutiu
    • , Giulia Iannelli
    •  & Nuno Maulide

  • Article |

    A new type of transformation converting a heteroaromatic carbon atom into a nitrogen atom, turning quinolines into quinazolines to enable manipulation of molecular properties, is reported.

    • Jisoo Woo
    • , Colin Stein
    •  & Mark D. Levin

  • News & Views |

    An unconventional route for modifying pharmaceutically relevant molecules swaps an atom of carbon for one of nitrogen. The resulting derivatives might open up avenues of research in medicinal-chemistry campaigns.

    • Filippo Ficarra
    •  & Mattia Silvi

  • Article |

    A new method is described that uses arenium-ion-catalysed halodealkylation of silanes with four alkyl groups, typically considered synthetic dead ends, to convert Me4Si and related quaternary silanes into orthogonally substituted (functionalized) silanes.

    • Tao He
    • , Hendrik F. T. Klare
    •  & Martin Oestreich

  • Article |

    We report a radical-based Ni/Ag-electrocatalytic cross-coupling of substituted carboxylic acids, enabling an approach to accessing complex molecular architectures, which relies on a silver additive that forms an active Ag nanoparticle-coated electrode surface along with carefully chosen ligands.

    • Benxiang Zhang
    • , Jiayan He
    •  & Phil S. Baran

  • News & Views |

    An organic light-emitting diode has been integrated with an optically driven organic laser to produce laser light from electricity. The design bypasses many of the challenges posed by direct electrical input in such devices.

    • Stéphane Kéna-Cohen

  • Research Briefing |

    The natural toxins portimine A and B have attracted interest for their unusual chemical architecture and potent anti-cancer activity. The first total synthesis of portimines enables the identification of portimine A’s molecular target and reveals that the toxin induces programmed cell death in human cancer cells.

  • Article |

    The synthesis and isolation of a crystalline dication derived from a bis(imino)carbene through a two-electron oxidation/oxide-ion abstraction strategy is reported that bypasses the carbene radical cation, maintaining significant electrophilicity with two accessible vacant orbitals.

    • Ying Kai Loh
    • , Mohand Melaimi
    •  & Guy Bertrand

  • Article |

    Heterogeneous geminal-atom catalysts, which pair single-atom sites in specific coordination and spatial proximity, offer a new avenue for the sustainable manufacture of fine chemicals.

    • Xiao Hai
    • , Yang Zheng
    •  & Jiong Lu

  • Article |

    A scalable total synthesis of portimines enables structural reassignment of portimine B and in-depth functional evaluation of portimine A, revealing that portimine A induces translation inhibition selectively in human cancer cells and is efficacious in vivo tumour-clearance models.

    • Junchen Tang
    • , Weichao Li
    •  & Phil S. Baran

  • Article
    | Open Access

    We report a small-organic-molecule oscillator that catalyses an independent chemical reaction in situ without impairing its oscillating properties, allowing the construction of complex systems enhancing applications in automated synthesis and systems and polymerization chemistry.

    • Matthijs ter Harmsel
    • , Oliver R. Maguire
    •  & Syuzanna R. Harutyunyan

  • Article
    | Open Access

    Irradiation of chiral Al-salen complexes with violet light demonstrates efficient deracemization of cyclopropanes, enabling reactivity and enantioselectivity to be regulated simultaneously, negating the requirement for tailored catalyst–substrate recognition motifs.

    • Carina Onneken
    • , Tobias Morack
    •  & Ryan Gilmour

  • News & Views |

    Energy released from molecules under strain can promote difficult chemical reactions. A practical method has been developed that uses an overlooked, highly strained compound to rapidly construct complex organic products.

    • Fahima I. M. Idiris
    •  & Christopher R. Jones

  • Research Briefing |

    A minimal but general method has been developed for catalysing many different cross-coupling reactions — those in which two chemical fragments are joined. It requires only the two substrate substances, a nickel salt as a catalyst precursor, a catalyst for light-driven redox reactions and, in some cases, a nitrogen-containing base.

  • Article |

    Quinuclidine-pyridone and sulfonamide-pyridone ligands enable transannular γ-methylene C–H arylation of cycloalkane carboxylic acids with a range of ring sizes, bringing us closer to molecular editing of saturated carbocycles.

    • Guowei Kang
    • , Daniel A. Strassfeld
    •  & Jin-Quan Yu

  • Article |

    The strained C6H6 isomer 1,2,3-cyclohexatriene and its derivatives participate in a host of reaction modes which demonstrate their potential for selective chemical transformations and provide an unconventional entryway to complex scaffolds.

    • Andrew V. Kelleghan
    • , Ana S. Bulger
    •  & Neil K. Garg

  • Research Briefing |

    A catalyst with a hydrophobic cavity that contains an active iron centre has been developed to convert methane into methanol. It has a ‘catch-and-release’ mechanism whereby a hydrophobic methane molecule enters the cavity for oxidation and the resulting hydrophilic methanol molecule is released into the surrounding aqueous solution.

  • Article |

    The synthesis of 1,3- and 1,2-disubstituted cubanes is achieved using a cyclobutadiene precursor and a photolytic carboxylation reaction, respectively, and copper-catalysed amination, arylation, alkylation and trifluoromethylation reactions have been developed enabling the use of cubanes as bioisosteres of benzenes in drug design.

    • Mario P. Wiesenfeldt
    • , James A. Rossi-Ashton
    •  & David W. C. MacMillan

  • Article |

    The enantioconvergent alkylation of oxygen nucleophiles is achieved using α-haloamides and a readily available copper catalyst, and the reaction proceeds under mild conditions in the presence of a wide variety of functional groups.

    • Caiyou Chen
    •  & Gregory C. Fu

  • Article |

    The chemoselective and enantioconvergent N-alkylation of aliphatic amines, including ammonia, is achieved using chiral tridentate anionic ligands and a copper catalyst; the method shows excellent enantioselectivity and functional-group tolerance.

    • Ji-Jun Chen
    • , Jia-Heng Fang
    •  & Xin-Yuan Liu

  • Article
    | Open Access

    The design, synthesis and characterization of a helically chiral triaryloxonium ion is reported, which is an example of a chiral non-racemic and configurationally stable molecule in which the oxygen atom is the sole stereogenic centre.

    • Owen Smith
    • , Mihai V. Popescu
    •  & Martin D. Smith

  • News & Views |

    The study of how chemical reactions work is key to the design of new reactions, but relies on hard work and expert knowledge. A machine-learning tool has been developed that could change the way this challenge is approached.

    • Danilo M. Lustosa
    •  & Anat Milo

  • Article |

    Mechanistic elucidation through currently available kinetic analysis is limited by mathematical approximations and human interpretation, here a deep neural network model has been trained to analyse ordinary kinetic data and automatically elucidate the corresponding mechanism class.

    • Jordi Burés
    •  & Igor Larrosa

  • Article |

    Installation of multiple C–O bonds by concurrent oxygenation of contiguous C–H bonds in a selective fashion is highly desirable, and this is achieved by repeated operation of a potent oxidative catalyst via electrophotocatalysis.

    • Tao Shen
    • , Yi-Lun Li
    •  & Tristan H. Lambert

  • News & Views |

    Truly general chemical reactions work well regardless of the structural features and functional groups in the starting molecule. A new screening protocol speeds up the identification of such reactions in the field of asymmetric catalysis.

    • Manuel J. Scharf
    •  & Benjamin List

  • News & Views |

    Efforts to probe the biological functions of carbohydrates have long been limited by the lack of such molecules with well-defined structures. An automated carbohydrate synthesizer has been developed that could remedy this.

    • Hanchao Cheng
    •  & Peng George Wang

  • News & Views |

    The ozonolysis reaction is a classic of organic synthesis, but involves the formation of potentially explosive reaction intermediates. A modern, safer spin on this process makes use of previously overlooked chemistry.

    • Vignesh Palani
    •  & Alison Wendlandt

  • Article |

     The analytical workflow outlined in this study allows multiple crude reaction mixtures to be analysed simultaneously, with substantial reductions in method development and analysis time, and maximizes the chances of finding catalytic systems with broad substrate scope.

    • Corin C. Wagen
    • , Spencer E. McMinn
    •  & Eric N. Jacobsen

  • Article |

    Oxidative cleavage of alkenes is achieved using nitroarenes and light irradiation as an alternative to using ozone to break the carbon–carbon bonds, avoiding the explosive intermediates formed with ozone.

    • Alessandro Ruffoni
    • , Charlotte Hampton
    •  & Daniele Leonori

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