Synthetic chemistry methodology articles within Nature

Featured

  • 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

  • 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

  • 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
    | 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

  • Article |

    A self-adjustive catalytic system with nickel under visible-light-driven redox reaction conditions provides a general method for carbon–(hetero)atom cross-coupling reactions and is demonstrated for nine different bond-forming reactions.

    • Indrajit Ghosh
    • , Nikita Shlapakov
    •  & Burkhard König

  • 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

  • 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

  • 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

  • Article |

    A new methodology for the discovery of chalcogenides by tuning the temperature and flux ratios of systems using mixed fluxes is demonstrated, leading to the synthesis of 30 new and unreported compounds or compositions.

    • Xiuquan Zhou
    • , Venkata Surya Chaitanya Kolluru
    •  & Mercouri G. Kanatzidis

  • 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

  • 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

  • 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 |

    A synthetic strategy for the stereoselective preparation of sulfinate esters and related sulfur stereogenic centres via asymmetric condensation expands the drug discovery toolbox for these compounds.

    • Xin Zhang
    • , Esther Cai Xia Ang
    •  & Choon-Hong Tan

  • 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

  • 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

Browse broader subjects

Browse Synthetic chemistry methodology across other nature.com journals