Emilien Le Saux


Last Name

Le Saux

First Name

Emilien

ORCID

0000-0003-1887-6687

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2024 - 20253
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Publications 1 - 3 of 3
  • Coupling of unactivated alkyl electrophiles using frustrated ion pairs
    Item type: Journal Article
    Roediger, Sven; Le Saux, Emilien; Boehm, Philip; et al. (2024)
    Nature
    Cross-electrophile coupling reactions have evolved into a major strategy for rapidly assembling important organic molecules1. Two readily accessible electrophiles are coupled to form new C-C bonds, providing a key advantage over traditional cross-coupling strategies that require the preformation of reactive organometallic species. Yet, the formation of C(sp3)-C(sp3) bonds that form the core of nearly all organic compounds remains highly challenging with current approaches, calling for the design of innovative new strategies. Here we report a distinct, transition-metal-free platform to form such bonds without the need for activating or stabilizing groups on the coupling partners. The reaction is enabled by an unusual single-electron transfer in a frustrated ion pair, and it can couple fragments containing functional groups that would be challenging in related transition-metal-catalysed processes. Moreover, we could further leverage this new mechanistic manifold in the design of other reactions, showing the broad potential of this type of reactivity. We anticipate that our results will provide a framework for further exploration of this reactivity pattern to tackle challenging problems in organic synthesis.
  • Palladium-Catalyzed Transfer Iodination from Aryl Iodides to Nonactivated C(sp³)–H Bonds
    Item type: Journal Article
    Le Saux, Emilien; Morandi, Bill (2025)
    Journal of the American Chemical Society
    We report a new strategy for the catalytic iodination of nonactivated C(sp 3)-H bonds. The method merges the concepts of shuttle and light-enabled palladium catalysis to employ aryl iodides as both hydrogen atom transfer reagents and iodine donors. A noncanonical Pd0/PdI catalytic cycle is harnessed to transfer iodine from a C(sp 2) to a C(sp 3)-H bond under mild conditions, which tolerate sensitive functional groups. This mechanism is also applied to implement a C(sp 3)-H thiolation that exploits reversible steps of the system.
  • Metal- and CO-Free Carbonylation of Alkyl Iodides
    Item type: Journal Article
    Le Saux, Emilien; Mathis , Maurus; Panizzolo , Giorgia; et al. (2025)
    Journal of the American Chemical Society
    We report a new method for the carbonylation of alkyl iodides under photochemical conditions. The process relies on a simple aryl formate reagent, synthesized in one step from readily available chemicals and capable of releasing CO along with a phenolate species in the presence of a mild base. The photoactivity of this phenolate is harnessed to activate alkyl iodides via single-electron transfer and generate alkyl radicals that add to CO and ultimately offer access to carboxylic acids and amides. This new, user-friendly procedure overcomes the typical need for CO gas and/or metal catalysts in carbonylation chemistry while being highly efficient and versatile to accommodate a variety of functional groups.
Publications 1 - 3 of 3