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Influence of N‑Substituents on the Adsorption Geometry of OH-Functionalized Chiral N‑Heterocyclic Carbenes

Dery, Shahar ; Bellotti, Peter ; Ben-Tzvi, Tzipora ; Freitag, Matthias ; Shahar, Tehila ; Cossaro, Albano ; Verdini, Alberto ; Floreano, Luca ; Glorius, Frank ; Gross, Elad

Langmuir, 2021-08, Vol.37 (33), p.10029-10035 [Periódico revisado por pares]

American Chemical Society

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  • Título:
    Influence of N‑Substituents on the Adsorption Geometry of OH-Functionalized Chiral N‑Heterocyclic Carbenes
  • Autor: Dery, Shahar ; Bellotti, Peter ; Ben-Tzvi, Tzipora ; Freitag, Matthias ; Shahar, Tehila ; Cossaro, Albano ; Verdini, Alberto ; Floreano, Luca ; Glorius, Frank ; Gross, Elad
  • É parte de: Langmuir, 2021-08, Vol.37 (33), p.10029-10035
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Adsorption of chiral molecules on heterogeneous catalysts is a simple approach for inducing an asymmetric environment to enable enantioselective reactivity. Although the concept of chiral induction is straightforward, its practical utilization is far from simple, and only a few examples toward the successful chiral induction by surface anchoring of asymmetric modifiers have been demonstrated so far. Elucidating the factors that lead to successful chiral induction is therefore a crucial step for understanding the mechanism by which chirality is transferred. Herein, we identify the adsorption geometry of OH-functionalized N-heterocyclic carbenes (NHCs), which are chemical analogues to chiral modifiers that successfully promoted α-arylation reactions once anchored on Pd nanoparticles. Polarized near-edge X-ray absorption fine structure (NEXAFS) measurements on Pd(111) revealed that NHCs that were associated with low enantioselectivity were characterized with a well-ordered structure, in which the imidazole ring was vertically positioned and the OH-functionalized side arms were flat-lying. OH-functionalized NHCs that were associated with high enantioselectivity revealed a disordered/flexible adsorption geometry, which potentially enabled better interaction between the OH group and the prochiral reactant.
  • Editor: American Chemical Society
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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