Para-Selective Cyanation of Arenes by H-Bonded Template.
DFT study
H-bonded template
cyanation
para-C−H activation
regioselectivity
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
04 Sep 2020
04 Sep 2020
Historique:
received:
19
03
2020
pubmed:
21
3
2020
medline:
21
3
2020
entrez:
21
3
2020
Statut:
ppublish
Résumé
The significance of site selective functionalization stands upon the superior selectivity, easy synthesis and diverse product utility. In this work, we demonstrate the para-selective introduction of versatile nitrile moiety, enabled by a detachable and reusable H-bonded auxiliary. The methodology holds its efficiency irrespective of substrate electronic bias. The conspicuous shift in the step energetics was probed by both experimental and computational mechanistic tools, which heralds the inception of para-deuteration. The synthetic impact of the methodology was highlighted with reusability of directing group and post synthetic modifications.
Identifiants
pubmed: 32196777
doi: 10.1002/chem.202001368
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11558-11564Subventions
Organisme : Science and Engineering Research Board
ID : SERB (CRG/2018/003951)
Organisme : National Natural Science Foundation of China
ID : 21973055
Organisme : Natural Science Foundation of Shandong Province
ID : ZR2019MB049
Organisme : Department of Science and Technology, Ministry of Science and Technology
ID : YSS/2014/000530
Informations de copyright
© 2020 Wiley-VCH GmbH.
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CCDC 1899052, 1942587 and 1837260 for 1o, 7 and DG4, respectively, contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre.