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Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates

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Abstract

The mild and efficient palladium-catalyzed ortho C(sp2)–H diversification of (NH)-free 2-substituted benzimidazole, quinazoline, and imidazopyridine is reported using hypervalent iodine as the key reagent. Acetoxy, aryl, iodide and nitro functional groups were introduced on the same substrate by simply shifting the reaction conditions in the presence of inorganic additives (Cs2CO3, I2, NaNO2) and the hypervalent iodine reagent (diacetoxyiodo)benzene (PIDA) under aerobic conditions. The combination of NaNO2 with PIDA was successfully employed in Pd-catalyzed C–H bond nitration to achieve a library of nitrated 1,3 N-heterocycles. This versatile ortho C(sp2)–H activation strategy features operational simplicity, short reaction times, and ample substrate possibilities, it requires no ligands or silver salts as additives, and it shows good tolerance of oxidation prone functional groups.

Graphical abstract: Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates

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Article information


Submitted
26 Nov 2019
Accepted
18 Dec 2019
First published
10 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Hypervalent iodine promoted ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates

M. Saha and A. R. Das, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02533B

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