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Directing Group-Free Regioselective meta-C−H Functionalization of Pyridines

Chakraborty, S and Biju, AT (2023) Directing Group-Free Regioselective meta-C−H Functionalization of Pyridines. In: Angewandte Chemie - International Edition .

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Official URL: https://doi.org/10.1002/anie.202300049


The pyridine core is among the most common motifs found in pharmaceuticals and agrochemicals. Consequently, the C−H functionalization of pyridine is a prized reaction, as it can help access a broad spectrum of valuable chemicals. However, the intrinsic electronic properties of pyridines hinder their meta-C−H functionalization, requiring drastic conditions affecting functional group compatibility. A synthetic manoeuvre to overcome this challenge involves the temporary conversion of pyridines into electron-rich intermediates and subsequent regioselective electrophilic functionalization. This was recently accomplished by a ring-opening ring-closing sequence via Zincke imine intermediates by McNally and co-workers, and a dearomatization-rearomatization sequence via oxazino-pyridine intermediates by the Studer group. The mildness and simplicity of these protocols enable them to work with complex molecular setups for synthesizing natural products and bioactive molecules.

Item Type: Journal Article
Publication: Angewandte Chemie - International Edition
Publisher: John Wiley and Sons Inc
Additional Information: The copyright for this article belongs to John Wiley and Sons Inc.
Keywords: Agricultural chemicals; Electronic properties; Pyridine; Synthesis (chemical), Broad spectrum; C-H functionalization; C�H activation; Directing groups; Drastic conditions; Electron-rich; Intrinsic electronics; Regio-selective; Trifluoromethylation; Valuable chemicals, Regioselectivity
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 29 Mar 2023 10:53
Last Modified: 29 Mar 2023 10:53
URI: https://eprints.iisc.ac.in/id/eprint/81176

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