Regiocontrolled Remote C−H Olefination of Small Heterocycles

Achieving site‐selective C−H functionalization of arene is a fundamental challenge, as it is mainly controlled by the electronic nature of the molecules. A chelation‐assisted C−H functionalization strategy overcomes the selectivity issues by utilizing distance and geometry of covalently attached dir...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-12, Vol.24 (68), p.17906-17910
Main Authors: Achar, Tapas Kumar, Ramakrishna, Kankanala, Pal, Tapas, Porey, Sandip, Dolui, Pravas, Biswas, Jyoti Prasad, Maiti, Debabrata
Format: Article
Language:English
Subjects:
Backbone
bifunctional
catalysis
Chelation
Chemistry
Covalence
C−H activation
Deactivation
Functional groups
nitrogen heterocycles
remote-selectivity
Selectivity
Substrates
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Summary:Achieving site‐selective C−H functionalization of arene is a fundamental challenge, as it is mainly controlled by the electronic nature of the molecules. A chelation‐assisted C−H functionalization strategy overcomes the selectivity issues by utilizing distance and geometry of covalently attached directing groups (DGs). This strategy requires stoichiometric DG installation/removal and a suitable functional group on which to tether the DG. Such strategies are ineffective for small heterocycles unless suitable functional groups are added. Moreover, heterocycles are not the judicious choice as substrates owing to the possibilities of catalyst deactivation. Inspired by recent developments, this work demonstrates the utilization of a chelating template backbone bearing covalently attached directing groups, which enables site‐selective remote C−H functionalization of heterocycles. The observed selectivity is the outcome of non‐covalent interactions between the heterocycles and bifunctional template backbone. Non‐covalent interactions could lead to site‐selective remote C−H bond functionalizations of small heterocycles utilizing bifunctional template intermolecularly.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201804351