Transition-Metal-Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10-Phenanthroline.
carboradical
hydrocarbonation
single-electron-transfer
sodium hydride
styrenes
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
28 Mar 2023
28 Mar 2023
Historique:
received:
08
10
2022
medline:
5
1
2023
pubmed:
5
1
2023
entrez:
4
1
2023
Statut:
ppublish
Résumé
A transition-metal-free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10-phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti-Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH-mediated reduction of 1,10-phenanthroline works as an electron donor and a hydrogen source.
Identifiants
pubmed: 36599804
doi: 10.1002/chem.202203143
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202203143Informations de copyright
© 2023 Wiley-VCH GmbH.
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We conducted the reaction of 1,10-phenanthroline and NaH, followed by quenching with water, however, dihydrophenanthroline was not obtained because of its instability. Instead, over-reduction product tetrahydrophenanthroline was obtained. See Scheme S5 for details.
We confirmed that acridine was reduced by NaH in 1,4-dioxane to form 9,10-dihydroacridine 9, see: Scheme S6.
Cyclic voltammetry (CV) experiments indicate that the reaction of 9,10-dihydroacridine with NaH generates an electron donor in situ.
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