Efficiency of the Free-Radical Hydrophosphonylation of Alkenes: The Photoinduced Reaction of Dimethyl H -Phosphonate with Enopyranoses as an Exemplary Case - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2013

Efficiency of the Free-Radical Hydrophosphonylation of Alkenes: The Photoinduced Reaction of Dimethyl H -Phosphonate with Enopyranoses as an Exemplary Case

Alessandro Dondoni
Samuele Staderini
  • Fonction : Auteur

Résumé

Free-radical hydrophosphonylation of alkenes by H-phosphonates has been reported by other groups to occur under harsh conditions. On the other hand, we demonstrate in this paper that the hydrophosphonylation of alkene functionalized carbohydrates (enopyranoses) by dimethyl H-phosphonate can be carried out with high efficiency under neutral conditions at room temperature and with short reaction times using UV/Vis light irradiation in the presence of a suitable photoinitiator. Indeed, a range of structurally different allyl C-glycosides and exo-glycals were transformed into the corresponding glycosylalkyl phosphonates that were isolated in excellent yields (88–98 %), except for one case (45 %). A mechanism similar to that of the free-radical photoinduced hydrothiolation of alkenes is proposed.

Domaines

Chimie

Dates et versions

hal-03552465 , version 1 (02-02-2022)

Identifiants

Citer

Alberto Marra, Alessandro Dondoni, Samuele Staderini. Efficiency of the Free-Radical Hydrophosphonylation of Alkenes: The Photoinduced Reaction of Dimethyl H -Phosphonate with Enopyranoses as an Exemplary Case. European Journal of Organic Chemistry, 2013, 2013 (24), pp.5370-5375. ⟨10.1002/EJOC.201300780⟩. ⟨hal-03552465⟩
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