Organocatalysis

Organocatalysis is a type of catalysis where the catalyst in the chemical reaction is an organic (non-metallic) compound. The catalysts operate both through the transient formation of covalent bonds, such as in enamine and imminium catalysis, as well as through non-covalent interactions, such as in hydrogen bonding catalysis.

Latest Research and Reviews

  • Research | | open

    Investigation of a reaction scope usually starts with the optimization for a model substrate. Here, the authors apply a time-efficient multi-substrate screening approach to identify a general organocatalyst for the Diels–Alder reaction of cyclopentadiene with α,β-unsaturated aldehydes.

    • Hyejin Kim
    • , Gabriela Gerosa
    • , Jonas Aronow
    • , Pinar Kasaplar
    • , Jie Ouyang
    • , Julia B. Lingnau
    • , Paul Guerry
    • , Christophe Farès
    •  & Benjamin List
  • Research | | open

    Selenium has emerged as a metalloid for the catalytic construction of C–N bonds; however no functionalisation of aromatic compounds has been developed yet. Here, the authors report the para-amination of phenols via two successive sigmatropic rearrangements of a redox versatile Se–N bond.

    • Dingyuan Yan
    • , Guoqiang Wang
    • , Feng Xiong
    • , Wei-Yin Sun
    • , Zhuangzhi Shi
    • , Yi Lu
    • , Shuhua Li
    •  & Jing Zhao
  • Research | | open

    Non-covalent glycosyl donor activation often requires high organocatalyst loadings. Here, the authors demonstrate that strain-release glycosylations can take place at very low thiourea catalyst loadings. In addition, the authors developed a one-pot multicatalytic strategy that can diversify glycosides rapidly.

    • Chunfa Xu
    •  & Charles C. J. Loh
  • Research | | open

    Metal-mediated activation of CO for C-C coupling reactions is a valuable approach to carbon monoxide valorization. Here, the authors use low-coordinate iron(II) complexes for the selective scission and homologation of CO affording unusual squaraines and iron carboxylates under mild conditions.

    • Helen R. Sharpe
    • , Ana M. Geer
    • , Laurence J. Taylor
    • , Benjamin M. Gridley
    • , Toby J. Blundell
    • , Alexander J. Blake
    • , E. Stephen Davies
    • , William Lewis
    • , Jonathan McMaster
    • , David Robinson
    •  & Deborah L. Kays
  • Research | | open

    Ring-opening polymerisation of amino acid N-carboxyanhydrides is an established route to polypeptides, but controlling the product distribution can require careful optimisation. Here, simple variation of the choice of initiator provides a general route to linear or cyclic polypeptides and under mild conditions.

    • Yu Zhang
    • , Renjie Liu
    • , Hua Jin
    • , Wenliang Song
    • , Rimesh Augustine
    •  & Il Kim
  • Research |

    Chiral tertiary aldols are encountered in a variety of biologically relevant molecules. Making these valuable compounds directly from unbiased ketones has proven to be extremely challenging. Now it has been shown that sub-ppm levels of in situ generated silylium-based organic Lewis acid catalysts can give quantitative product formation in very high enantiopurity through a Mukaiyama aldol reaction.

    • Han Yong Bae
    • , Denis Höfler
    • , Philip S. J. Kaib
    • , Pinar Kasaplar
    • , Chandra Kanta De
    • , Arno Döhring
    • , Sunggi Lee
    • , Karl Kaupmees
    • , Ivo Leito
    •  & Benjamin List
    Nature Chemistry 10, 888-894

News and Comment

  • News and Views |

    Control over the length and composition of polymers is key to controlling their properties. Now, a photoswitchable catalyst is shown to allow external control over reaction rates, chain lengths and even polymer composition in ring-opening polymerizations.

    • Paula K. Kuroishi
    •  & Andrew P. Dove
    Nature Catalysis 1, 486-487
  • News and Views |

    Catalytic methods are among the most valuable tools for sustainable synthesis. Domino catalysis enables multiple reactions to be combined so that synthetic efficiency may begin to approach that of nature, but significant challenges remain before this promising approach can fulfil the needs of pharmaceutical and materials chemistry.

    • Thomas Broja
    • , Patrick J. W. Fuchs
    •  & Kirsten Zeitler
    Nature Chemistry 7, 950-951
  • News and Views |

    Preparing powerful reactive intermediates such as enolates and homoenolates for C–C bond formation used to require strong bases and stoichiometric reagents. They can now be catalytically generated from α-functionalized aldehydes or even from saturated esters under mild conditions using N-heterocyclic carbene catalysts.

    • Jeffrey W. Bode
    Nature Chemistry 5, 813-815