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Title

Chemo‐ and Regioselective Multiple C(sp2)−H Insertions of Malonate Metal Carbenes for Late‐Stage Functionalizations of Azahelicenes
Authors
Nikolova, Yana
Fabri, Bibiana
Moneva Lorente, Pau
Guarnieri Ibanez, Alejandro José
de Aguirre, Adiran
Soda, Yoshiki
Pescitelli, Gennaro
Zinna, Francesco
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Published in Angewandte Chemie. International edition in English. 2022, vol. 61, no. 41, e202210798
Abstract Chiral quinacridines react up to four times, step-by-step, with α-diazomalonates under RuII and RhII catalysis. By selecting the catalyst, [CpRu(CH3CN)3][PF6] (Cp=cyclopentadienyl) or Rh2(oct)4, chemo and regioselective insertions of derived metal carbenes are achieved in favor of mono- or bis-functionalized malonate derivatives, respectively, (r.r.>49 : 1, up to 77 % yield, 12 examples). This multi-introduction of malonate groups is particularly useful to tune optical and chemical properties such as absorption, emission or Brønsted acidity but also cellular bioimaging. Density-functional theory further elucidates the origin of the carbene insertion selectivity and also showcases the importance of conformations in the optical response.
Keywords Carbenes — C−H Insertion — Helicenes — Late-Stage Functionalization — Photophysical Properties
Identifiers
PMID: 35943860
Full text
Article (Published version) (6 MB) - public document Free access
Other version: https://onlinelibrary.wiley.com/doi/10.1002/anie.202210798
Dataset: https://doi.org/10.26037/yareta:py3o7ztvrnfdtcatka6yfrz27e
Structures
Faculté des sciences / Section de chimie et biochimie / Département de chimie minérale, analytique et appliquée
Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Faculté des sciences / Section de chimie et biochimie / Département de biochimie
Research groups Groupe Lacour
Groupe Poblador Bahamonde
Project
European Commission: HEL4CHIROLED
Citation
(ISO format) 		NIKOLOVA, Yana et al. Chemo‐ and Regioselective Multiple C(sp2)−H Insertions of Malonate Metal Carbenes for Late‐Stage Functionalizations of Azahelicenes. In: Angewandte Chemie. International edition in English, 2022, vol. 61, n° 41, p. e202210798. doi: 10.1002/anie.202210798 https://archive-ouverte.unige.ch/unige:164073

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Deposited on : 2022-10-10

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