Transition-Metal-Free C2-Functionalization of Pyridines through Aryne Three-Component Coupling

Guin, A and Bhattacharjee, S and Biju, AT (2021) Transition-Metal-Free C2-Functionalization of Pyridines through Aryne Three-Component Coupling. In: Chemistry - A European Journal .

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Abstract

The direct C2-functionalization of pyridines through a transition-metal-free protocol by using aryne multicomponent coupling is demonstrated. The reaction allowed a broad-scope synthesis of C2-substituted pyridine derivatives bearing the �CF3 group in good yields with α,α,α-trifluoroacetophenones as the third component. Activated keto esters could also be employed as the third component in this formal 1,2-di(hetero)arylation of ketones. Performing the reaction under dilute conditions inhibited the competing pyridine�aryne polymerization pathway. Nucleophilic attack by the initially generated pyridylidene intermediate on the carbonyl followed by an SNAr process resembling the Smiles rearrangement affords the desired products. © 2021 Wiley-VCH GmbH

Item Type:	Journal Article
Publication:	Chemistry - A European Journal
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	21 Nov 2021 16:28
Last Modified:	21 Nov 2021 16:28
URI:	http://eprints.iisc.ac.in/id/eprint/69935

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