Organic chemistry articles within Nature

Featured

  • News & Views |

    A compound made by plants used in traditional medicine has been prepared by chemical synthesis, providing enough for biological testing. The unexpected finding that it acts at opioid receptors raises prospects for drug discovery.

    • Nicholas P. R. Onuska
    •  & Joshua G. Pierce

  • News Feature |

    A retracted paper highlights chemistry’s history of trying to avoid the expensive, toxic — but necessary — catalyst.

    • Ariana Remmel

  • Research Briefing |

    Carbon–carbon single bonds are found in most organic molecules. A new electrocatalytic method can create such bonds by uniting different alkyl carboxylic acids, substantially shortening synthetic routes to useful molecules. The reaction uses inexpensive reagents in a simple and scalable set-up, and allows the inclusion of many other functional groups.

  • Article |

    A synthetic route to GB18, an alkaloid from the bark of hallucinogenic Galbulimima sp., is developed, enabling its identification as an antagonist of κ- and μ-opioid receptors.

    • Stone Woo
    •  & Ryan A. Shenvi

  • Article
    | Open Access

    A study demonstrates that nitrous oxide can act as the source of O in a catalytic conversion of aryl halides to phenols, releasing N2 as by-product.

    • Franck Le Vaillant
    • , Ana Mateos Calbet
    •  & Josep Cornella

  • Article |

    A biocatalytic enzyme originating from bacteria, EneIRED, facilitates amine-activated conjugate alkene reduction followed by reductive amination, efficiently preparing chiral amine diastereomers, which are commonly used in pharmaceuticals and agrochemicals. 

    • Thomas W. Thorpe
    • , James R. Marshall
    •  & Nicholas J. Turner

  • Article |

    An Ni-electrocatalytic system can couple two different carboxylates using doubly decarboxylative cross-coupling, tolerating a range of functional groups, being scalable, used for the synthesis of 32 known compounds and reducing overall step counts by 73%.

    • Benxiang Zhang
    • , Yang Gao
    •  & Phil S. Baran

  • News & Views |

    Chemical synthesis often relies on reactions catalysed by transition metals. Electrochemical methods have now been developed that negate this need, opening up pathways to previously challenging reactions.

    • Charlotte Willans

  • Article |

    Carbene chemistry is used to introduce difluoromethyl groups labelled with fluorine-18 into compounds for positron emission tomography imaging, using a reagent designed for high molar activity and versatility.

    • Jeroen B. I. Sap
    • , Claudio F. Meyer
    •  & Véronique Gouverneur

  • Article |

    An electrochemical method is used to couple together two alkyl halides, enabling efficient cross-electrophile coupling of a variety of alkyl electrophiles with improved chemoselectivity compared with existing methods.

    • Wen Zhang
    • , Lingxiang Lu
    •  & Song Lin

  • Article |

    Identification of a hyperstable boronate enables automated lego-like synthesis to access a wider range of three-dimensionally complex small organic molecules rich in Csp3–C bonds. 

    • Daniel J. Blair
    • , Sriyankari Chitti
    •  & Martin D. Burke

  • News & Views |

    Benzene rings are almost unbreakable in typical reaction conditions. Chemistry has now been developed that selectively breaks these rings open, highlighting their potential as building blocks for making open-chain molecules.

    • Mark R. Crimmin

  • Article |

    Enantioselective supramolecular recognition allows for the asymmetric synthesis of nitrogen stereocentres, providing chiral ammonium cations in a dynamic crystallization process.

    • Mark P. Walsh
    • , Joseph M. Phelps
    •  & Matthew O. Kitching

  • Article |

    A metallaphotoredox-based cross-coupling platform is capable of activating a wide range of free alcohols using N-heterocyclic carbene salts, cleaving C–O bonds to form free carbon radicals that are then used to form new C–C bonds.

    • Zhe Dong
    •  & David W. C. MacMillan

  • Article |

    Common aromatic rings, such as anilines, arylboronic acids and aryl halides, can be opened up and converted to alkenyl nitriles through carbon–carbon bond cleavage using a copper catalyst.

    • Xu Qiu
    • , Yueqian Sang
    •  & Ning Jiao

  • Article |

    Selective borylation of azines—nitrogen-containing aromatic heterocycles used in the synthesis of many pharmaceuticals—is made possible by forming a radical from an aminoborane using a photocatalyst.

    • Ji Hye Kim
    • , Timothée Constantin
    •  & Daniele Leonori

  • Article |

    Nitrogen is ‘deleted’ from secondary amines using anomeric amide reagents, which react with the amine to form an isodiazene, after which nitrogen gas is released and the resulting carbon radicals combine to form a carbon–carbon bond.

    • Sean H. Kennedy
    • , Balu D. Dherange
    •  & Mark D. Levin

  • News & Views |

    Many scientific fields and industries rely on the synthesis of small organic molecules. A chemical reagent has been developed that allows such molecules to be made by ‘deleting’ nitrogen atoms from readily accessible precursors.

    • William P. Unsworth
    •  & Alyssa-Jennifer Avestro

  • News & Views |

    An accessible machine-learning tool has been developed that can accelerate the optimization of a wide range of synthetic reactions — and reveals how cognitive bias might have undermined optimization by humans.

    • Jason E. Hein

  • Article |

    Metal-free borylation of C(sp3)–H bonds by violet-light-induced hydrogen atom transfer is reported, demonstrating high selectivity for the substitution of methyl C–H bonds over other weaker C–H bonds.

    • Chao Shu
    • , Adam Noble
    •  & Varinder K. Aggarwal

  • Article |

    A synthetic route-planning algorithm, augmented with causal relationships that allow it to strategize over multiple steps, can design complex natural-product syntheses that are indistinguishable from those designed by human experts.

    • Barbara Mikulak-Klucznik
    • , Patrycja Gołębiowska
    •  & Bartosz A. Grzybowski

  • Article |

    In a rotating reactor, immiscible or pairwise-immiscible liquids organize into stable but internally agitated concentric layers, enabling multistep syntheses and separations of reaction mixtures.

    • Olgierd Cybulski
    • , Miroslaw Dygas
    •  & Bartosz A. Grzybowski

  • Article |

    An iron complex sequentially activates N2 and C–H bonds in benzene to form aniline, with coupling achieved through partial silylation of a reduced iron–nitrogen complex and phenyl migration.

    • Sean F. McWilliams
    • , Daniël L. J. Broere
    •  & Patrick L. Holland

  • News & Views |

    Molecules have previously been made that induce protein destruction inside cells. A new class of molecule now induces the degradation of membrane and extracellular proteins — opening up avenues for drug discovery.

    • Claire Whitworth
    •  & Alessio Ciulli

  • Article |

    Lysosome-targeting chimaeras—in which a small molecule or antibody is connected to a glycopeptide ligand to form a conjugate that can bind a cell-surface lysosome-shuttling receptor and a protein target—are used to achieve the targeted degradation of extracellular and membrane proteins.

    • Steven M. Banik
    • , Kayvon Pedram
    •  & Carolyn R. Bertozzi

  • Article |

    A prebiotic synthesis of the purine DNA nucleosides (deoxyadenosine and deoxyinosine) in which the pyrimidine RNA nucleosides (cytidine and uridine) persist has implications for the coexistence of DNA and RNA at the dawn of life.

    • Jianfeng Xu
    • , Václav Chmela
    •  & John D. Sutherland

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