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Hypervalent iodine promoted: Ortho diversification: 2-aryl benzimidazole, quinazoline and imidazopyridine as directing templates
M. Saha,
Published in Royal Society of Chemistry
PMID: 31922163
Volume: 18
Issue: 5
Pages: 941 - 955
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. © 2020 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetOrganic and Biomolecular Chemistry
PublisherData powered by TypesetRoyal Society of Chemistry