Jump to main content
Jump to site search

Issue 23, 2018
Previous Article Next Article

Metal-free C(sp2)–H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination

Author affiliations

Abstract

The direct C2−H oxidation and imination of a wide variety of azoles was achieved by using a commercially available simple K2CO3/I2 reagent combination. The iodinated azole adduct, produced via the in situ generation of N-heterocyclic carbene, is the key intermediate for C2−H oxidation, imination, and amination of azoles. Significantly, these reactions proceed under mild conditions with high to excellent yields, are scalable to large quantity and exhibit a broad substrate scope. Interestingly, this direct C2−H imination method allowed us to access various pharmacologically active N6-alkyl or N6-aryl substituted benzimidazoquinazolinone scaffolds through intramolecular C−H imination in a sequential one-pot reaction.

Graphical abstract: Metal-free C(sp2)–H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination

Back to tab navigation

Supplementary files

Publication details

The article was received on 02 Mar 2018, accepted on 03 Apr 2018 and first published on 03 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00535D
Citation: Org. Biomol. Chem., 2018,16, 4243-4260
  •   Request permissions

    Metal-free C(sp2)–H functionalization of azoles: K2CO3/I2-mediated oxidation, imination, and amination

    R. Das, M. Banerjee, R. K. Rai, R. Karri and G. Roy, Org. Biomol. Chem., 2018, 16, 4243
    DOI: 10.1039/C8OB00535D

Search articles by author

Spotlight

Advertisements